Ortho-substituted phenylacetamides

ABSTRACT

Ortho-substituted phenylacetamides I ##STR1## (R 1  =H, alkyl, cycloalkyl, alkenyl, alkynyl, phenylalkynyl, alkoxyalkyl, alkoxycarbonyl, phenyl, phenylalkyl, phenylalkenyl or phenoxyalkyl, 5- or 6-membered heterocycle with 1-3 hetero atoms to which a benzene ring or a 5- or 6-membered heterocycle can be fused; R 2  and R 3  =H, CN, halogen, alkyl, alkoxy; R 4  and R 5  =H, alkyl and R 4  or R 5  =alkoxy; Y═O, S, SO, SO 2 , N═N, O--CO, CO--O, CO--O--CH 2 , alkylene or haloalkylene, alkenylene, alkynylene, oxy- alkylene, thio-alkylene, alkyleneoxy, carbonylalkylene or alkylenecarbonyl, W=alkoxyimino, alkoxymethylene or alkylthiomethylene), excepting compounds where R 1  is hydrogen, phenyl or 2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropyl, R 2  to R 5  are each hydrogen, Y is carbonyloxymethylene and W is methoxymethylene or methylthiomethylene, 
     are suitable as fungicides and for controlling pests.

This is a division of application Ser. No. 08/124,437 filed on Sep. 22, 1993, now U.S. Pat. No. 5,395,854, which is a continuation of application Ser. No. 07/751,955 filed on Aug. 29, 1991, now abandoned.

The present invention relates to novel ortho-substituted phenylacetamides of the formula I ##STR2## where

R¹ is hydrogen, C₁ -C₁₈ -alkyl, C₃ -C₈ -cycloalkyl which can have from one to three substituents selected from a group of 3 halogen atoms, 3 C₁ -C₄ -alkyl groups, a partially or completely halogenated C₁ -C₄ -alkenyl group and a phenyl group which can carry one or two halogen atoms and/or one C₁ -C₄ -alkyl group and/or one C₁ -C₄ -alkoxy group, or is C₂ -C₁₀ -alkenyl, C₂ -C₄ -alkynyl which can carry a phenyl radical, or is C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, C₁ -C₄ -alkoxycarbonyl, phenyl, phenyl-C₁ -C₄ -alkyl or phenyl-C₂ -C₄ -alkenyl or phenoxy-C₁ -C₄ -alkyl where each aromatic ring can have from one to five substituents selected from a group of 2 nitro radicals, 2 cyano radicals, 5 halogen atoms and in each case three of the following: C₁ -C₄ -alkyl, partially or completely halogenated C₁ -C₄ -alkyl, C₂ -C₄ -alkenyl, partially or completely halogenated C₂ -C₄ -alkenyl and C₁ -C₄ -alkoxy, and of one phenyl, benzyl, phenoxy, benzyloxy or phenylthio radical, where the last two radicals in turn can have one or two of the following substituents: cyano, halogen or C₁ -C₄ -alkyl;

a 5- or 6-membered heterocycle with from one to three hetero atoms selected from a group of two oxygen, two sulfur and three nitrogen atoms, excepting compounds with two adjacent oxygen and/or sulfur atoms, it being possible for a benzene ring or a 5- or 6-membered heteroaromatic ring with one nitrogen, oxygen or sulfur atom to be fused on to the heterocycle, and it being possible for the heterocycle to carry one halogen atom, one or two C₁ -C₄ -alkyl radicals or one phenyl radical;

R² and R³ are each, independently of one another, hydrogen, cyano, halogen, C₁ -C₄ -alkyl or C₁ -C₄ -alkoxy;

R⁴ and R⁵ are each, independently of one another, hydrogen or C₁ -C₄ -alkyl or one of the two is C₁ -C₄ -alkoxy;

Y is oxygen, sulfur, --SO--, --SO₂ --, --CH₂ --O--SO₂ --, --N═N--, --O--CO, --CO--O-- or --CO--O--CH₂ --, C₁ -C₄ -alkylene which can be partially or completely halogenated and can carry one of the following: cyano, nitro, C₁ -C₄ -alkyl, partially or completely halogenated C₁ -C₄ -alkyl, C₂ -C₄ -alkenyl, partially or completely halogenated C₂ -C₄ -alkenyl, C₁ -C₄ -alkoxy, phenyl or phenoxy, it being possible for the last two radicals in turn to have one or two of the following substituents: cyano, halogen or C₁ -C₄ -alkyl, C₂ -C₄ -alkenylene or C₂ -C₄ -alkynylene, oxy-(C₁ -C₄)-alkylene, thio-(C₁ -C₄)-alkylene or C₁ -C₄ -alkyleneoxy or carbonyl-(C₁ -C₄)-alkylene or C₁ -C₄ -alkylenecarbonyl;

W is C₁ -C₄ -alkoxyimino, C₁ -C₄ -alkoxymethylene or C₁ -C₄ -alkylthiomethylene,

excepting compounds where R¹ is hydrogen, phenyl or 2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropyl, R² to R⁵ are each hydrogen, Y is carbonyloxymethylene and W is methoxymethylene or methylthiomethylene.

The present invention also relates to processes for preparing these compounds, to their use as fungicides and to their use as insecticides, nematicides and acaricides and to fungicidal agents and agents for controlling pests which contain these compounds as active substances.

EP-A 310 954 discloses, inter alia, fungicidal ortho-substituted phenylacetamides of the type of compounds I, and their phenylacetonitrile precursors, where R¹ is hydrogen, phenyl or 2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropyl, R² to R⁵ are each hydrogen, Y is carboxymethylene and W is methoxymethylene or methylthiomethylene. European patent 398 692 discloses similar compounds.

It is an object of the present invention to find novel fungicidal ortho-substituted phenylacetic acid derivatives and novel insecticidal, acaricidal and nematicidal active ingredients.

We have found that this object is achieved by the ortho-substituted phenylacetamides of the formula I defined above.

The specific meanings of the substituents in the novel compounds I are as follows:

R¹

hydrogen;

branched or unbranched C₁ -C₁₈ -alkyl such as methyl, ethyl, n-propyl, isopropyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl n-butyl, sec-butyl, isobutyl, tert-butyl, 3-methylbutyl, n-pentyl, n-hexyl, n-heptyl, 2,6-dimethylheptyl, n-octyl, n-nonyl, n-decyl, n-pentadecyl, n-heptadecyl and n-octadecyl, preferably C₁ -C₁₀ -alkyl;

C₃ -C₈ -cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl, each of which can have from one to three substituents selected from a group of 3 halogen atoms such as fluorine, chlorine, bromine and iodine, especially fluorine and chlorine, 3 C₁ -C₄ -alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, and tert-butyl, partially or completely halogenated C₁ -C₄ -alkenyl such as 2,2-dichloroethenyl, and phenyl which can carry one or two halogen atoms as mentioned above, especially fluorine and chlorine, and/or one C₁ -C₄ -alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl and tert-butyl and/or one C₁ -C₄ -alkoxy group such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy and tert-butoxy; cyclopropyl, 1-methylcyclopropyl, 2,2-dichlorocyclopropyl, 1-(2,2-dichlorovinyl)cyclopropyl, 1-phenylcyclopropyl, 1-(p-fluorophenyl)cyclopropyl, cyclohexyl and 1-methylcyclohexyl are preferred;

C₂ -C₁₀ -alkenyl such as vinyl, allyl, 1-propenyl, 2-propenyl, 2-methylpropenyl, 2-butenyl, 1-methylpropenyl, 3-methyl-2-butenyl, 1,3-pentadienyl, 2,6-dimethyl-5-heptenyl and 2,6-dimethyl-1,5-heptadienyl;

C₂ -C₄ -alkynyl such as ethynyl and 2-propynyl, which can carry a phenyl radical, eg. 2-phenylethynyl;

C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl such as methoxymethyl, ethoxymethyl, n-propoxymethyl, isopropoxymethyl, n-butoxymethyl, tert-butoxymethyl, 1-methoxyethyl, 2-methoxyethyl, 1-ethoxyethyl, 2-ethoxyethyl and 2-n-propoxyethyl;

C₁ -C₄ -alkoxycarbonyl such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl and tert-butoxycarbonyl, preferably methoxycarbonyl

phenyl, phenyl-C₁ -C₄ -alkyl such as benzyl, phenethyl, 3-phenyl-n-propyl and 4-phenyl-n-butyl, phenyl-C₂ -C₄ -alkenyl such styryl and 2-phenyl-2-propenyl or phenoxy-C₁ -C₄ -alkyl such as phenoxymethyl, 2-phenoxyethyl, 3-phenoxypropyl and 4-phenoxybutyl, it being possible for each of the said groups to carry on the phenyl ring a total of from one to five radicals, in particular:

one or two nitro groups,

one or two cyano groups,

up to 5 halogen atoms as mentioned above, especially fluorine and chlorine,

up to 3 C₁ -C₄ -alkyl groups as mentioned above,

up to 3 partially or completely halogenated C₁ -C₄ -alkyl groups such as fluoromethyl, chloromethyl, trifluoromethyl, trichloromethyl, dichlorofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl,2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl, especially trifluoromethyl,

up to 3 C₂ -C₄ -alkenyl groups such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl and 2-methyl-2-propenyl, especially ethenyl and 2-propenyl,

up to 3 partially or completely halogenated C₂ -C₄ -alkenyl groups such as 2-fluoroethenyl, 2-chloroethenyl, trifluoroethenyl, trichloroethenyl and 2-chloro-2-propenyl and

up to 3 C₁ -C₄ -alkoxy groups such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy and tert-butoxy,

phenyl, benzyl, phenoxy, benzyloxy or phenylthio, each of which in turn can have one or two of the following substituents: cyano, halogen as mentioned above, especially fluorine and chlorine, or C₁ -C₄ -alkyl as mentioned above;

phenyl, 2-nitrophenyl, 4-nitrophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 2-iodophenyl, 2,3-dichlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2,3,4-trichlorophenyl, 2,3,5-trichlorophenyl, 2,3,6-trichlorophenyl, 3,4,5-trichlorophenyl, pentafluorophenyl, pentachlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 3-isopropylphenyl, 4-isopropylphenyl, 3-tert-butylphenyl, 4-tert-butylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 4-tert-butyl-2-methylphenyl, 3,5-diethylphenyl, 2,3,5-trimethylphenyl, 2,4,6-trimethylphenyl, 4-cyclohexylphenyl, 3-phenoxyphenyl, 4-phenoxyphenyl, 4-phenylthiophenyl, 3-benzyloxyphenyl, 4-benzyloxyphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 2-chloromethylphenyl, 3-chloromethylphenyl, 4-chloromethylphenyl, benzyl, 4-chlorobenzyl, phenethyl, 4-chlorophenethyl, styryl, 4-chlorostyryl, phenoxy, 2-chlorophenoxy, 3-chlorophenoxy, 4-chlorophenoxy, 2-methylphenoxy, 3-methylphenoxy, 4-methylphenoxy, 2-trifluoromethylphenoxy, 3-trifluoromethylphenoxy, 4-trifluoromethylphenoxy, phenoxymethyl and 2-phenoxyethyl are preferred;

a 5- or 6-membered heterocycle with from one to three hetero atoms selected from a group of two oxygen, two sulfur and three nitrogen atoms, excepting compounds with two adjacent oxygen and/or sulfur atoms, it being possible for a benzene ring or a 5- or 6-membered heteroaromatic ring with a nitrogen, oxygen or sulfur atom to be fused on to the heterocycle, for example 2-pyrrolyl, 3-pyrrolyl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-benzoxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, benzothiazol-2-yl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-thiadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,2,4-triazol-3-yl, 1,3,4-triazol-2-yl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidyl, 4-pyrimidyl, 5-pyrimidyl, 2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl,

it being possible for the heterocycles to carry a halogen atom as mentioned above, especially fluorine and chlorine, one or two C₁ -C₄ -alkyl groups as mentioned above, especially methyl, or a phenyl radicals, for example 5-chlorobenzothiazol-2-yl, 6-chloro-2-pyridyl, 6-methyl-2-pyridyl, 6-ethyl-2-pyridyl, 6-n-propyl-2-pyridyl, 6-isopropyl-2-pyridyl, 6-n-butyl-2-pyridyl, 6-sec-butyl-2-pyridyl and 6-tert-butyl-2-pyridyl, 6-phenyl-2-pyridyl and 4,8-dimethyl-2-quinolyl; halophenyl, C₁ -C₄ -alkylphenyl, di-(C₁ -C₄)-alkylphenyl and benzothiazol-2-yl are particularly preferred;

R², R³

hydrogen, cyano, halogen as mentioned above, especially fluorine and chlorine,

branched or unbranched C₁ -C₄ -alkyl as mentioned above, especially methyl, ethyl and isopropyl;

C₁ -C₄ -alkoxy as mentioned above, especially methoxy; hydrogen is particularly preferred;

R⁴, R⁵

hydrogen,

branched or unbranched C₁ -C₄ -alkyl as mentioned above, especially methyl, ethyl, n-propyl and n-butyl;

one of the two substituents is C₁ -C₄ -alkoxy as mentioned above, especially methoxy;

Y

oxygen or sulfur;

--SO--, --SO₂ --, --CH₂ --O--SO₂ --, --N═N--m --O--CO--, --CO--O-- or --CO--O--CH₂ --, preferably --O--CO--, --CO--O-- and --CO--O--CH₂ --;

C₁ -C₄ -alkylene which can be partially or completely halogenated, especially fluorinated or chlorinated, and which can also carry one of the following: cyano, nitro, C₁ -C₄ -alkyl as mentioned above, partially or completely halogenated C₁ -C₄ -alkyl as mentioned above, C₂ -C₄ -alkenyl as mentioned above, partially or completely halogenated C₂ -C₄ -alkenyl as mentioned above, C₁ -C₄ -alkoxy as mentioned above, phenyl or phenoxy, it being possible for the latter two radicals in turn to have one or two of the following substituents: cyano, halogen as mentioned above, especially fluorine and chlorine, or C₁ -C₄ -alkyl as mentioned above, especially methyl; methylene or ethylene is preferred;

C₂ -C₄ -alkenylene such as ethenylene, 2-propenylene and 2-butenylene, preferably ethenylene;

C₂ -C₄ -alkynylene such as ethynylene, 2-propynylene and 2-butynylene, preferably ethynylene;

oxy-(C₁ -C₄)-alkylene such as oxymethylene, oxyethylene, oxy-n-propylene and oxy-n-butylene, preferably oxymethylene;

thio-(C₁ -C₄)-alkylene such as thiomethylene, thioethylene, thio-n-propylene and thio-n-butylene, preferably thiomethylene;

C₁ -C₄ -alkyleneoxy such as methyleneoxy, ethyleneoxy, n-propyleneoxy and n-butyleneoxy, preferably methyleneoxy;

carbonyl-(C₁ -C₄)-alkylene such as carbonylmethylene, carbonylethylene, carbonyl-n-propylene and carbonyl-n-butylene, preferably carbonylmethylene;

C₁ -C₄ -alkylenecarbonyl such as methylenecarbonyl, ethylenecarbonyl, n-propylenecarbonyl and n-butylenecarbonyl, preferably methylenecarbonyl;

carbonyloxy-(C₁ -C₄)-alkylene such as carbonyloxymethylene, carbonyloxyethylene, carbonyloxy-n-propylene and carbonyloxy-n-butylene, preferably carbonyloxymethylene;

W

C₁ -C₄ -alkoxyimino such as methoxyimino, ethoxyimino, n-propoxyimino, isopropoxyimino, n-butoxyimino, sec-butoxyimino and tert-butoxyimino, preferably methoxyimino;

C₁ -C₄ -alkoxymethylene such as methoxymethylene, ethoxymethylene, n-propoxymethylene, isopropoxymethylene, n-butoxymethylene, sec-butoxymethylene and tert-butoxymethylene, preferably methoxymethylene;

C₁ -C₄ -alkylthiomethylene such as methylthiomethylene, ethylthiomethylene, n-propylthiomethylene, isopropylthiomethylene, n-butylthiomethylene, sec-butylthiomethylene and tert-butylthiomethylene, preferably methylthiomethylene;

C₁ -C₄ -alkoxyimino is preferred.

Particularly suitable ortho-substituted phenylacetamides I are shown in Table 1, with compounds with R² and R³ each being hydrogen, R⁴ being methyl, R⁵ being hydrogen and W being methoxyimino or methoxymethylene being particularly preferred. Very particularly suitable are 2-methoxyimino-2-[2-(o-methylphenoxymethyl)phenyl]-acetic acid N-methylamide and 2-methoxyimino-2-[2-(o-methylphenoxymethyl)phenyl] acetic acid N-methoxyamide.

Preparation of compounds I may result in E/Z isomer mixtures where the two isomers differ by the alkoxy or alkylthio of the substituent W being cis or trans to the amide moiety. If required, the isomers can be separated by conventional methods, eg. by crystallization or chromatography. Compounds with the E configuration (alkoxy or alkylthio of the substituent W trans to the amide moiety) are particularly preferred.

The ortho-substituted phenylacetamides I can be obtained in a variety of ways, preferably by one of the following methods:

a) reaction of phenylacetic acid derivatives II with amines II ##STR3## L is halogen, especially chlorine and bromine, or C₁ -C₄ -alkoxy, especially methoxy.

Preparation of ortho-substituted phenylacetamides I where R⁴ or R⁵ is C₁ -C₄ -alkoxy preferably starts from a phenylacetyl chloride II (L=Cl).

The reaction is normally carried out by conventional methods (eg. Organikum, 16th edition 1985, pages 409-412) in an inert solvent or diluent, advantageously in the presence of a base.

Particularly suitable solvents or diluents are chlorohydrocarbons such as dichloromethane, ethers such as dioxane, and alcohols such as methanol and ethanol.

Examples of suitable bases are alkali metal hydroxides such as sodium and potassium hydroxide, alkali metal carbonates such as sodium and potassium carbonate, alkali metal alcoholates such as sodium methylate and sodium ethylate, especially tertiary amines such as triethylamine and heteroaromatic amines such as pyridine and 4-dimethylaminopyridine. However, it is also possible to use the amine III itself as base, for complete reaction in not less than the stoichiometric amount based on II.

All the starting compounds are expediently employed in approximately the stoichiometric ratio, but in some cases an excess of one component, of up to about 10 mol %, may be advisable.

If the amine III is used as base, it is present in a larger excess.

The reaction is generally carried out at from 0° to 120° C., in particular at the boiling point of the solvent.

If L is halogen, the reaction can also be carried out in a 2-phase system with phase-transfer catalysis. It is possible and advantageous to use for this mixture of a chlorohydrocarbon such as methylene chloride, aqueous alkali, eg. sodium hydroxide solution, and a phase-transfer catalyst such as tetra-n-butylammonium hydroxide. In this case, the reaction is carried out at, for example, from 10° C. to the boiling point of one of the components of the solvent mixture.

The reaction is normally carried out under atmospheric pressure. An increase or reduction in the pressure is possible but generally has no advantages.

Phenylacetic acid derivatives II where L is halogen are known or can be prepared by known processes (eg. Organikum, 16th edition 1985, pages 415, 622 and 423).

The phenylacetic acid derivatives II where L is C₁ -C₄ -alkoxy are disclosed in EP-A 178 826 and EP-A 226 917 (X==CH-O-alkyl), EP-A 244 077 (X==CH-S-alkyl) and EP-A 253 213 and EP-A 254 426 (X==N-O-alkyl) or can be prepared by similar processes.

For example, the phenylacetic acid derivatives II with Y=oxymethylene, thiomethylene or --CO--O--CH₂ -- are obtained by nucleophilic substitution on benzyl halides VI ##STR4## b) Hydrolysis of phenylacetonitriles IV ##STR5##

The hydrolysis of the phenylacetronitriles IV is normally catalyzed by acid or base by conventional methods [cf., for example, Beckwith in: Zabicky The Chemistry of Amides, pages 119 to 125 (1970) and Synthesis, 243 (1980)] in an inert solvent or diluent.

Particularly suitable solvents are alcohols such as tert-butanol and ethylene glycol.

Particularly suitable acids are concentrated mineral acids such as hydrochloric acid, sulfuric acid and phosphoric acid, and preferred bases are alkali metal hydroxides such as sodium and potassium hydroxide.

The reaction is normally carried out at from 0° to 200° C., in particular from 20° C. to the boiling point of the solvent.

The statements made for method (a) apply to the ratios of amounts and the pressure.

Phenylacetonitriles of the formula IV are disclosed, for example, in EP-A 310 954 or can be prepared by the methods described therein.

The ortho-substituted phenylacetamides I where R⁴ and R⁵ are each hydrogen can be alkylated on the amide nitrogen by conventional processes [eg. Challis in: Zabicky The Chemistry of Amides, pages 731-857 (1970)]: ##STR6## Alk is C₁ -C₄ -alkyl, X is halogen, especially bromine and iodine.

This normally entails conversion of the phenylacetamides I where R⁴ and R⁵ are each hydrogen, in an inert solvent or diluent, with a base into the anions and reaction of the latter with an alkyl halide, preferably an alkyl iodide.

Particularly suitable solvents or diluents are ethers such as tetrahydrofuran and dioxane.

Particularly suitable bases are alkali metal hydroxides such as sodium and potassium hydroxide and alkali metal hydrides such as sodium and potassium hydride.

The reaction is generally carried out at from 0° to 100° C., in particular at the boiling point of the solvent.

The statements made for method (a) apply to the ratio of amounts and the pressure.

The ortho-substituted phenylacetamides I are suitable as fungicides and for controlling pests such as insects, nematodes and acarids.

The ortho-substituted phenylacetamides I have excellent activity against a wide spectrum of fungi which are pathogenic for plants, especially from the classes of Ascomycetes and Basidiomycetes. Some of them have systemic activity and can be employed as leaf and soil fungicides.

They are particularly important for controlling a large number of fungi on various crops such as wheat, rye, barley, oats, rice, corn, grass, cotton, soybean, coffee, sugarcane, grapevines, fruit and ornamental plants and vegetables such as cucumbers, beans and pumpkins, and on the seeds of these plants.

They are particularly suitable for controlling the following plants diseases:

Erysiphe graminis (powdery mildew) in cereals,

Erysiphe cichoracearum and Sphaerotheca fuliginea on pumpkins,

Podosphaera leucotricha on apples,

Uncinula necator on grapevines,

Puccinia species on cereals,

Rhizoctonia species on cotton and lawns,

Ustilago species on cereals and sugarcane,

Venturia inaequalis (scab) on apples,

Helminthosporium species on cereals,

Septoria nodorum on wheat,

Botrytis cinerea (gray mold) on strawberries, grapevines,

Cercospora arachidicola on peanuts,

Pseudocercosporella herpotrichoides on wheat, barley,

Pyricularia oryzae on rice,

Phytophthora infestans on potatoes and tomatoes,

Fusarium and Verticillium species on various plants,

Plasmopara viticola on grapevines,

Alternaria species on vegetables and fruit.

The compounds are applied by treating the fungi or the plants, seeds, materials or soil to be protected from fungal attack with a fungicidal amount of the active ingredients. The application is carried out before or after infection of the materials, plants or seeds by the fungi.

The ortho-substituted phenylacetamides I are also suitable for controlling pests from the classes of insects, arachnids and nematodes. They can be employed as pesticides in crop protection and in the hygiene, store protection and veterinary sectors.

The insect pests include:

from the order of Lepidoptera, for example Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholita funebrana, Grapholita molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keifferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malcosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flamea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scarbra, Plutella xylostella, Pseudoplusia includens, Phyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerelella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis;

from the order of Coleoptera, for example Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Onlema oryzae, Otiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophilus granaria;

from the order of Diptera, for example Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glossia morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea and Tipula paludosa;

from the order of Thysanoptera, for example Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci;

from the order of Hymenoptera, for example Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta;

from the order of Heteroptera, for example Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euchistus impictinventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis and Thyanta perditor;

from the order of Homoptera, for example Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicoryne brassicae, Cerosipha gossypii, Dreyfusia nordmannianae, Dreyfusia piceae, Dyasphis radicola, Dysaulacorthum pseudosolani, Empoasca fabae, Macrosiphum avenae, Macrosiphum eurphorbiae, Macrosiphon rosae, Megoura viciae, Metopolophium, dirhodum, Myzodes persicae, Myzus cerasi, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Trialeurodes vaporariorum and Viteus vitifolii;

from the order of Isoptera, for example Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus and Termes natalensis;

from the order of Orthoptera, for example Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus birittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus and Tachycines asynamorus;

from the class of Arachnoidea, for example arachnids (Acarina) such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoenicis, Bryobia praetiosa, Dermacentor silvarum, Eotetranychus carpini, Eriophyes sheldoni, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobins megnini, Paratetranychus pilosus, Permanyssus gallinae, Phyllocaptrata oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae;

from the class of nematodes, for example root knot nematodes, eg. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, eg. Globodera rostochiensis, Heterodera avenae, Heterodera glycinae, Heterodera schatii, Heterodera triflolii, stem and leaf eelworms, eg. Belonolaimus longicaudatus, Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchus multicinctus, Longidorus elongatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivus, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus and Pratylenchus goodeyi.

The active ingredients can be converted into conventional formulations such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application forms depend on the purposes for which they are used; they ought in every case to ensure fine and uniform distribution of the ortho-substituted phenylacetamide. The formulations are prepared in a conventional manner, eg. by extending the active ingredient with solvents and/or carriers, if required using emulsifiers and dispersants, it being possible to use other organic solvents as auxiliary solvents when water is used as diluent.

Suitable for preparing directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point such as kerosine or diesel oil, also coaltar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg. benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or derivatives thereof, methanol, ethanol, propanol, butanol, chloroform, tetrachloromethane, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, highly polar solvents, eg. dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone and water.

Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances can be homogenized, as such or dissolved in an oil or solvent, using wetting agents, adhesion promoters, dispersants or emulsifiers in water. However, concentrates suitable for dilution with water can also be prepared from active substance, wetting agent, adhesion promoter, dispersant or emulsifier and, possibly, solvent or oil.

Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of ligninsulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates and fatty acids and their alkali metal and alkaline earth metal salts, salts of sulfated fatty alcohol glycol ethers, products of the condensation of sulfonates naphthalene and naphthalene derivatives with formaldehyde, products of the condensation of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ether, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol ester, lignin sulfite waste liquors and methylcellulose.

Powders and dusting and broadcasting agents can be prepared by mixing or grinding together the active substances with a solid carrier.

The concentrations of active ingredient in the formulations ready for use can vary within wide limits.

The agents very generally contain from 0.0001 to 95, preferably from 0.01 to 90, % by weight of active ingredient.

Formulations containing more than 95% by weight of active ingredient can be applied very successfully by the ultra low volume (ULV) method, in which case even the active ingredient without additives can be used.

Examples of such formulations are:

I. a solution of 90 parts by weight of compounds No. 87 and 10 parts by weight of N-methyl-α-pyrrolidone, which is suitable for application in the form of very small drops;

II. a mixture of 20 parts by weight of compounds No. 93, 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid N-monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonates, 5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil; a fine dispersion of the solution in water is used;

III. An aqueous dispersion of 20 parts by weight of compounds No. 133, 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil;

IV. an aqueous dispersion of 20 parts by weight of compound No. 242, 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction of boiling point 210° to 280° C. and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil;

V. a mixture, ground in a hammer mill, of 80 parts by weight of compound No. 252, 3 parts by weight of sodium diisobutylnaphthalene-α-sulfonate, 10 parts by weight of the sodium salt of a ligninsulfonic acid from a sulfite waste liquor and 7 parts by weight of powdered silica gel; a fine dispersion of the mixture in water can be sprayed;

VI. an intimate mixture of 3 pats by weight of compound No. 449 and 97 parts by weight of finely divided kaolin; this dusting agent contains 3% by weight of active ingredient;

VII. an intimate mixture of 30 parts by weight of compound No. 494, 92 parts by weight of powdered silica gel and 8 parts by weight of liquid paraffin which has been sprayed on to the surface of this silica gel; this formulation makes the active ingredient adhere well;

VIII. a stable aqueous dispersion of 40 parts by weight of compounds No. 585, 10 parts by weight of the sodium salt of a phenolsulfonic acid/urea/formaldehyde condensate, 2 parts by weight of silica gel and 48 parts by weight of water, which can be further diluted;

IX. a stable oily dispersion of 20 parts by weight of compound No. 587, 2 parts by weight of calcium dodecylbenzenesulfonate, 8 parts by weight of fatty alcohol polyglycol ether, 20 parts by weight of the sodium salt of a phenolsulfonic acid/urea/formaldehyde condensate and 68 parts by weight of a liquid paraffin.

Granules, eg. coated, impregnated or homogeneous granules, can be prepared by binding the active ingredients to solid carriers. Examples of solid carriers are mineral earths such as silica gel, silicic acids, silicates, talc, kaolin, attapulgite, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.

The application rates in fungicidal agents depend on the nature of the desired effect and range from 0.02 to 3 kg of active ingredient per ha. The novel compounds can also be used to protect materials (wood), eg. against Paecilomyces variotii.

For treating seeds, in general from 0.001 to 50 g, preferably 0.01 to 10 g, of active ingredient are required per kilogram of seeds.

The application rate for controlling insects in the open is from 0.02 to 10, preferably 0.1 to 2.0 kg/ha active ingredient.

In these application forms, the novel agents can also be mixed with other active ingredients, eg. with herbicides, insecticides, growth regulators, fungicides or fertilizers. These agents can be added to the novel agents in the ratio of from 1:10 to 10:1 by weight, where appropriate just before application (tank mix). Mixing with fungicides or insecticides in many cases results in an extension of the spectrum of action.

The agents and the formulations prepared therefrom ready for use, such as solutions, emulsions, suspensions, powders, dusts, pastes or granules, are applied in a conventional manner, for example by spraying, atomizing, dusting, broadcasting, treating seeds or watering.

PREPARATION EXAMPLES EXAMPLE 1

2-Methoxyimino-2-[2-(m-chlorophenoxymethyl)phenyl]acetamide ##STR7##

7.0 g (23 mmol) of 2-methoxyimino-2-[2-(m-chlorophenoxymethyl)phenyl]acetonitrile were added to a mixture of 50 ml of glycol and 10 ml of a 25% by weight aqueous solution of potassium hydroxide, and the reaction mixture was then heated at 80° C. for 2 hours. The solid was then separated off, washed with methyl tert-butyl ether and dried. Yield: 58%;

¹ H-NMR (in CDCl₃, TMS as standard): d=4.00(s,3H); 5.18(s,2H); 6.10(sbr,1H); 6.75(sbr,1H); 6.78(d,1H); 6.92(m,2H); 7.10-7.50(m,5H).

EXAMPLE 2

2-Methoxyimino-2-[2-(o,p-dimethylphenoxymethyl)phenyl]acetic acid N-methylamide ##STR8##

0.465 g (15 mmol) of monomethylamine dried over potassium hydroxide was passed at about 25° C. into a solution of 5.0 g (15 mmol) of 2-methoxyimino-2-[2-(o,p-dimethylphenoxymethyl)phenyl]acetyl chloride in 30 ml of dichloromethane. This mixture was stirred for one hour and then diluted with 70 ml of dichloromethane. By-products were extracted with 100 ml of water and then the organic phase was worked up in a conventional manner to give the product. Yield: 88% (oil);

¹ H-NMR (in CDCl₃, TMS as standard): d=2.20(s,3H); 2.25(s,3H); 2.90(d,3H); 3.94(s,3H); 4.93(s,2H); 6.70-7.60(m,7H).

EXAMPLE 3

2-Methoxyimino-2-(2-benzyloxyphenyl)acetic acid N,N-dimethylamide ##STR9##

A solution of 4.9 g (16.4 mmol) of methyl 2-methoxyimino-2-(2-benzyloxyphenyl)acetate and 0.9 g (20 mmol) of dimethylamine in 20 ml of methanol was stirred at about 25° C. for 60 hours. After removal of the solvent, the crude product was purified by chromatography on silica gel (methyl tert-butyl ether/n-hexane mixture as eluent). Yield: 66%;

¹ H-NMR (in CDCl₃, TMS as standard): d=3.38(s,3H); 3.49(s,3H); 4.01(s,3H); 5.03(s,2H); 6.90-7.10(m,2H); 7.30-7.40(m,6H); 8.75(d,1H).

EXAMPLE 4

2-Methoxyimino-2-[2-(o,p-dimethylphenoxymethyl)phenyl]acetic acid N,N-dimethylamide ##STR10##

0.675 g (15 mmol) of dried dimethylamine was reacted with 5.0 g (15 mmol) of 2-methoxyimino-2-[2-(o,p-dimethylphenoxymethyl)phenyl]acetyl chloride in a similar manner to Example 2. Yield: 78% (oil);

¹ H-NMR (in CDCl₃, TMS as standard): d=2.20(s,3H); 2.23(s,3H); 3.02(s,3H); 3.18(s,3H); 3.95(s,3H); 5.02(s,2H); 6.60-7.60(m,7H).

Further final products I which were or can be prepared in the same way are listed in Table 1.

                                      TABLE                                        __________________________________________________________________________      ##STR11##                                             I (R.sup.2,                                                                    R.sup.3 = H)            No.                                                                               Y       R.sup.1         R.sup.4                                                                            R.sup.5                                                                           W      Physical data                         __________________________________________________________________________      1 CH.sub.2                                                                               H               H   H  NOCH.sub.3                                    2 CHCl    H               H   H  NOCH.sub.3                                    3 CHBr    H               H   H  NOCH.sub.3                                    4 CHI     H               H   H  NOCH.sub.3                                    5 CH.sub.2CH.sub.2                                                                       C.sub.6 H.sub.5 H   H  NOCH.sub.3                                    6 CH.sub.2CH.sub.2                                                                       2-FC.sub.6 H.sub.4                                                                             H   H  NOCH.sub.3                                    7 CH.sub.2CH.sub.2                                                                       3-FC.sub.6 H.sub.4                                                                             H   H  NOCH.sub.3                                    8 CH.sub.2CH.sub.2                                                                       4-FC.sub.6 H.sub.4                                                                             H   H  NOCH.sub.3                                    9 CH.sub.2CH.sub.2                                                                       2-ClC.sub.6 H.sub.4                                                                            H   H  NOCH.sub.3                                    10                                                                               CH.sub.2CH.sub.2                                                                       3-ClC.sub.6 H.sub.4                                                                            H   H  NOCH.sub.3                                    11                                                                               CH.sub.2CH.sub.2                                                                       4-ClC.sub.6 H.sub.4                                                                            H   H  NOCH.sub.3                                    12                                                                               CH.sub.2CH.sub.2                                                                       2-BrC.sub.6 H.sub.4                                                                            H   H  NOCH.sub.3                                    13                                                                               CH.sub.2CH.sub.2                                                                       4-BrC.sub.6 H.sub.4                                                                            H   H  NOCH.sub.3                                    14                                                                               CH.sub.2CH.sub.2                                                                       2-IC.sub.6 H.sub.4                                                                             H   H  NOCH.sub.3                                    15                                                                               CH.sub.2CH.sub.2                                                                       2-CH.sub.3C.sub.6 H.sub.4                                                                      H   H  NOCH.sub.3                                    16                                                                               CH.sub.2CH.sub.2                                                                       3-CH.sub.3C.sub.6 H.sub.4                                                                      H   H  NOCH.sub.3                                    17                                                                               CH.sub.2CH.sub.2                                                                       4-CH.sub.3C.sub.6 H.sub.4                                                                      H   H  NOCH.sub.3                                    18                                                                               CH.sub.2CH.sub.2                                                                       2-OCH.sub.3C.sub.6 H.sub.4                                                                     H   H  NOCH.sub.3                                    19                                                                               CH.sub.2CH.sub.2                                                                       3-OCH.sub.3C.sub.6 H.sub.4                                                                     H   H  NOCH.sub.3                                    20                                                                               CH.sub.2CH.sub.2                                                                       4-OCH.sub.3C.sub.6 H.sub.4                                                                     H   H  NOCH.sub.3                                    21                                                                               CH.sub.2CH.sub.2                                                                       2-CF.sub.3C.sub.6 H.sub.4                                                                      H   H  NOCH.sub.3                                    22                                                                               CH.sub.2CH.sub.2                                                                       3-CF.sub.3C.sub.6 H.sub.4                                                                      H   H  NOCH.sub.3                                    23                                                                               CH.sub.2CH.sub.2                                                                       4-CF.sub.3C.sub.6 H.sub.4                                                                      H   H  NOCH.sub.3                                    24                                                                               CH.sub.2CH.sub.2                                                                       2,4-Cl.sub.2C.sub.6 H.sub.3                                                                    H   H  NOCH.sub.3                                    25                                                                               CH.sub.2CH.sub.2                                                                       2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                            H   H  NOCH.sub.3                                    26                                                                               CH.sub.2CH.sub.2                                                                       2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2                                                          H   H  NOCH.sub.3                                    27                                                                               CH.sub.2CH.sub.2                                                                       Pyridin-3-yl    H   H  NOCH.sub.3                                    28                                                                               CH.sub.2CH.sub.2                                                                       Furan-2-yl      H   H  NOCH.sub.3                                    29                                                                               CH.sub.2CH.sub.2                                                                       6-CH.sub.3 -Pyridin-2-yl                                                                       H   H  NOCH.sub.3                                    30                                                                               CH.sub.2CH.sub.2                                                                       Benzothiazol-2-yl                                                                              H   H  NOCH.sub.3                                    31                                                                               CHCH    C.sub.6 H.sub.5 H   H  NOCH.sub.3                                    32                                                                               CHCH    2-FC.sub.6 H.sub.4                                                                             H   H  NOCH.sub.3                                    33                                                                               CHCH    3-FC.sub.6 H.sub.4                                                                             H   H  NOCH.sub.3                                    34                                                                               CHCH    4-FC.sub.6 H.sub.4                                                                             H   H  NOCH.sub.3                                    35                                                                               CHCH    2-ClC.sub.6 H.sub.4                                                                            H   H  NOCH.sub.3                                    36                                                                               CHCH    3-ClC.sub.6 H.sub.4                                                                            H   H  NOCH.sub.3                                    37                                                                               CHCH    4-ClC.sub.6 H.sub.4                                                                            H   H  NOCH.sub.3                                    38                                                                               CHCH    2-BrC.sub.6 H.sub.4                                                                            H   H  NOCH.sub.3                                    39                                                                               CHCH    4-BrC.sub.6 H.sub.4                                                                            H   H  NOCH.sub.3                                    40                                                                               CHCH    2-IC.sub.6 H.sub.4                                                                             H   H  NOCH.sub.3                                    41                                                                               CHCH    2-CH.sub.3C.sub.6 H.sub.4                                                                      H   H  NOCH.sub.3                                    42                                                                               CHCH    3-CH.sub.3C.sub.6 H.sub.4                                                                      H   H  NOCH.sub.3                                    43                                                                               CHCH    4-CH.sub.3C.sub.6 H.sub.4                                                                      H   H  NOCH.sub.3                                    44                                                                               CHCH    2-OCH.sub.3C.sub.6 H.sub.4                                                                     H   H  NOCH.sub.3                                    45                                                                               CHCH    3-OCH.sub.3C.sub.6 H.sub.4                                                                     H   H  NOCH.sub.3                                    46                                                                               CHCH    4-OCH.sub.3C.sub.6 H.sub.4                                                                     H   H  NOCH.sub.3                                    47                                                                               CHCH    2-CF.sub.3C.sub.6 H.sub.4                                                                      H   H  NOCH.sub.3                                    48                                                                               CHCH    3-CF.sub.3C.sub.6 H.sub.4                                                                      H   H  NOCH.sub.3                                    49                                                                               CHCH    4-CF.sub.3C.sub.6 H.sub.4                                                                      H   H  NOCH.sub.3                                    50                                                                               CHCH    2,4-Cl.sub.2C.sub.6 H.sub.3                                                                    H   H  NOCH.sub.3                                    51                                                                               CHCH    2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                            H   H  NOCH.sub.3                                    52                                                                               CHCH    2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2                                                          H   H  NOCH.sub.3                                    53                                                                               CHCH    Pyridin-3-yl    H   H  NOCH.sub.3                                    54                                                                               CHCH    Furan-2-yl      H   H  NOCH.sub.3                                    55                                                                               CHCH    6-CH.sub.3 Pyridin-2-yl                                                                        H   H  NOCH.sub.3                                    56                                                                               CHCH    Benzothiazol-2-yl                                                                              H   H  NOCH.sub.3                                    57                                                                               CH.sub.2 O                                                                             C.sub.6 H.sub.5 H   H  NOCH.sub.3                                    58                                                                               CH.sub.2 O                                                                             2-FC.sub.6 H.sub.4                                                                             H   H  NOCH.sub.3                                    59                                                                               CH.sub.2 O                                                                             3-FC.sub.6 H.sub.4                                                                             H   H  NOCH.sub.3                                    60                                                                               CH.sub.2 O                                                                             4-FC.sub.6 H.sub.4                                                                             H   H  NOCH.sub.3                                    61                                                                               CH.sub.2 O                                                                             2-ClC.sub.6 H.sub.4                                                                            H   H  NOCH.sub.3                                    62                                                                               CH.sub.2 O                                                                             3-ClC.sub.6 H.sub.4                                                                            H   H  NOCH.sub.3                                    63                                                                               CH.sub.2 O                                                                             4-ClC.sub.6 H.sub.4                                                                            H   H  NOCH.sub.3                                    64                                                                               CH.sub.2 O                                                                             2-BrC.sub.6 H.sub. 4                                                                           H   H  NOCH.sub.3                                    65                                                                               CH.sub.2 O                                                                             4-BrC.sub.6 H.sub.4                                                                            H   H  NOCH.sub.3                                    66                                                                               CH.sub.2 O                                                                             2-IC.sub.6 H.sub.4                                                                             H   H  NOCH.sub.3                                    67                                                                               CH.sub.2 O                                                                             2-CH.sub.3C.sub.6 H.sub.4                                                                      H   H  NOCH.sub.3                                    68                                                                               CH.sub.2 O                                                                             3-CH.sub.3C.sub.6 H.sub.4                                                                      H   H  NOCH.sub.3                                    69                                                                               CH.sub.2 O                                                                             4-CH.sub.3C.sub.6 H.sub.4                                                                      H   H  NOCH.sub.3                                    70                                                                               CH.sub.2 O                                                                             2-OCH.sub.3C.sub.6 H.sub.4                                                                     H   H  NOCH.sub.3                                    71                                                                               CH.sub.2 O                                                                             3-OCH.sub.3C.sub.6 H.sub.4                                                                     H   H  NOCH.sub.3                                    72                                                                               CH.sub.2 O                                                                             4-OCH.sub.3C.sub.6 H.sub.4                                                                     H   H  NOCH.sub.3                                    73                                                                               CH.sub.2 O                                                                             2-CF.sub.3C.sub.6 H.sub.4                                                                      H   H  NOCH.sub.3                                    74                                                                               CH.sub.2 O                                                                             3-CF.sub.3C.sub.6 H.sub.4                                                                      H   H  NOCH.sub.3                                    75                                                                               CH.sub.2 O                                                                             4-CF.sub.3C.sub.6 H.sub.4                                                                      H   H  NOCH.sub.3                                    76                                                                               CH.sub.2 O                                                                             2,4-(Cl.sub.2C.sub.6 H.sub.3                                                                   H   H  NOCH.sub.3                                    77                                                                               CH.sub.2 O                                                                             2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                            H   H  NOCH.sub.3                                    78                                                                               CH.sub.2 O                                                                             2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2                                                          H   H  NOCH.sub.3                                    79                                                                               CH.sub.2 O                                                                             Pyridin-3-yl    H   H  NOCH.sub.3                                    80                                                                               CH.sub.2 O                                                                             Furan-2-yl      H   H  NOCH.sub.3                                    81                                                                               CH.sub.2 O                                                                             6-CH.sub.3 -Pyridin-2-yl                                                                       H   H  NOCH.sub.3                                    82                                                                               CH.sub.2 O                                                                             Benzothiazol-2-yl                                                                              H   H  NOCH.sub.3                                    83                                                                               OCH.sub.2                                                                              H               H   H  NOCH.sub.3                                    84                                                                               OCH.sub.2                                                                              C.sub.6 H.sub.5 H   H  NOCH.sub.3                                    85                                                                               OCH.sub.2                                                                              2-FC.sub.6 H.sub.4                                                                             H   H  NOCH.sub.3                                    86                                                                               OCH.sub.2                                                                              3-FC.sub.6 H.sub.4                                                                             H   H  NOCH.sub.3                                    87                                                                               OCH.sub.2                                                                              4-FC.sub.6 H.sub.4                                                                             H   H  NOCH.sub.3                                                                            M.p.127-9° C.;IR(KBr):3371                                              ,3184,1652,1507,                                                               1249,1050,824 cm.sup.-1                88                                                                               OCH.sub.2                                                                              2-ClC.sub.6 H.sub.4                                                                            H   H  NOCH.sub.3                                    89                                                                               OCH.sub.2                                                                              3-ClC.sub.6 H.sub.4                                                                            H   H  NOCH.sub.3                                                                            M.p.104-5° C.;IR(KBr):3416                                              ,1663,1559,1482,                                                               1249,1045,904,775 cm.sup.-1            90                                                                               OCH.sub.2                                                                              4-ClC.sub.6 H.sub.4                                                                            H   H  NOCH.sub.3                                                                            M.p.105-10° C.                  91                                                                               OCH.sub.2                                                                              2-BrC.sub.6 H.sub.4                                                                            H   H  NOCH.sub.3                                                                            M.p.88-90° C.;1H-NMR(CDCl.                                              sub.3): δ=4.13                                                           (s,3H),5.35(s2H),6.85(m,2H),7.25(                                              m,1H),7.58                                                                     (m,3H),7.78(d,1H),7.86(d,1H)           92                                                                               OCH.sub.2                                                                              4-BrC.sub.6 H.sub.4                                                                            H   H  NOCH.sub.3                                    93                                                                               OCH.sub.2                                                                              2-IC.sub.6 H.sub.4                                                                             H   H  NOCH.sub.3                                                                            M.p.148-50° C.;IR(KBr):337                                              3,1652,1474,1249,                                                              1055,749                               94                                                                               OCH.sub.2                                                                              2-CH.sub.3C.sub.6 H.sub.4                                                                      H   H  NOCH.sub.3                                    95                                                                               OCH.sub.2                                                                              3-CH.sub.3C.sub.6 H.sub.4                                                                      H   H  NOCH.sub.3                                    96                                                                               OCH.sub.2                                                                              4-CH.sub.3C.sub.6 H.sub.4                                                                      H   H  NOCH.sub.3                                                                            M.p.100-2° C.;IR(KBr):1674                                              ,1510,1239,1042,                                                               814                                    97                                                                               OCH.sub.2                                                                              2-OCH.sub.3C.sub.6 H.sub.4                                                                     H   H  NOCH.sub.3                                    98                                                                               OCH.sub.2                                                                              3-OCH.sub.3C.sub.6 H.sub.4                                                                     H   H  NOCH.sub.3                                    99                                                                               OCH.sub.2                                                                              4-OCH.sub.3C.sub.6 H.sub.4                                                                     H   H  NOCH.sub.3                                   100                                                                               OCH.sub.2                                                                              2-CF.sub.3C.sub.6 H.sub.4                                                                      H   H  NOCH.sub.3                                   101                                                                               OCH.sub.2                                                                              3-CF.sub.3C.sub.6 H.sub.4                                                                      H   H  NOCH.sub.3                                   102                                                                               OCH.sub.2                                                                              4-CF.sub.3C.sub.6 H.sub.4                                                                      H   H  NOCH.sub.3                                   103                                                                               OCH.sub.2                                                                              2,4-Cl.sub.2C.sub.6 H.sub.3                                                                    H   H  NOCH.sub.3                                   104                                                                               OCH.sub.2                                                                              2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                            H   H  NOCH.sub.3                                   105                                                                               OCH.sub.2                                                                              2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2                                                          H   H  NOCH.sub.3                                   106                                                                               OCH.sub.2                                                                              2-CH.sub.3 -4-ClC.sub.6 H.sub.3                                                                H   H  NOCH.sub.3                                   107                                                                               OCH.sub.2                                                                              3-t-C.sub.4 H.sub.9C.sub.6 H.sub.4                                                             H   H  NOCH.sub.3                                   108                                                                               OCH.sub.2                                                                              4-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                               H   H  NOCH.sub.3                                   109                                                                               OCH.sub.2                                                                              2-Cl, 4-CH.sub.3C.sub.6 H.sub.3                                                                H   H  NOCH.sub.3                                   110                                                                               OCH.sub.2                                                                              Pyridin-2-yl    H   H  NOCH.sub.3                                   111                                                                               OCH.sub.2                                                                              6-CH.sub.3 -Pyridin-2-yl                                                                       H   H  NOCH.sub.3                                   112                                                                               OCH.sub.2                                                                              2-Cl-Pyridin-2-yl                                                                              H   H  NOCH.sub.3                                   113                                                                               OCH.sub.2                                                                              Benzothiazol-2-yl                                                                              H   H  NOCH.sub.3                                   114                                                                               O       H               H   H  NOCH.sub.3                                   115                                                                               O       C.sub.6 H.sub.5 H   H  NOCH.sub.3                                   116                                                                               O       3-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                               H   H  NOCH.sub.3                                   117                                                                               O       3-OC.sub.3 H.sub.4C.sub.6 H.sub.4                                                              H   H  NOCH.sub.3                                   118                                                                               O       Pyridin-2-yl    H   H  NOCH.sub.3                                   119                                                                               O       6-C.sub.6 H.sub.5 -Pyridin-2-yl                                                                H   H  NOCH.sub.3                                   120                                                                               O       CH.sub.2CHCH.sub.2                                                                             H   H  NOCH.sub.3                                   121                                                                               O       3-C.sub.6 H.sub.5 OC.sub.6 H.sub.4                                                             H   H  NOCH.sub.3                                   122                                                                               O       3-C.sub.6 H.sub.5 SC.sub.6 H.sub.4                                                             H   H  NOCH.sub.3                                   123                                                                               O       3-C.sub.6 H.sub.5 CH.sub.2 OC.sub.6 H.sub.4                                                    H   H  NOCH.sub.3                                   124                                                                               CC      CH.sub.3        H   H  NOCH.sub.3                                   125                                                                               CC      C.sub.6 H.sub.5 H   H  NOCH.sub.3                                   126                                                                               S       C.sub.6 H.sub.5 H   H  NOCH.sub.3                                   127                                                                               S       2-Cl C.sub.6 H.sub.4                                                                           H   H  NOCH.sub.3                                   128                                                                               SCH.sub.2                                                                              C.sub.6 H.sub.5 H   H  NOCH.sub.3                                   129                                                                               SCH.sub.2                                                                              4-ClC.sub.6 H.sub.4                                                                            H   H  NOCH.sub.3                                   130                                                                               SCH.sub.2                                                                              4-CH.sub.3C.sub.6 H.sub.4                                                                      H   H  NOCH.sub.3                                   131                                                                               SCH.sub.2                                                                              6-CH.sub.3 -Pyridin-2-yl                                                                       H   H  NOCH.sub.3                                   132                                                                               SCH.sub.2                                                                              6-Cl-Pyridin-2-yl                                                                              H   H  NOCH.sub.3                                   133                                                                               SCH.sub.2                                                                              Benzothiazol-2-yl                                                                              H   H  NOCH.sub.3                                                                            M.p.171-8° C.;IR(KBr):3388                                              ,3155,1672,1650,                                                               1429,1037,989,748 cm.sup.-1           134                                                                               SCH.sub.2                                                                              5-Cl-Benzothiazol-2-yl                                                                         H   H  NOCH.sub.3                                   135                                                                               SCH.sub.2                                                                              6-Cl-Benzothiazol-2-yl                                                                         H   H  NOCH.sub.3                                   136                                                                               COO     CH.sub.3        H   H  NOCH.sub.3                                   137                                                                               COO     C.sub.6 H.sub.5 H   H  NOCH.sub.3                                   138                                                                               OCO     CH.sub.3        H   H  NOCH.sub.3                                   139                                                                               OCO     C.sub.6 H.sub.5 H   H  NOCH.sub.3                                   140                                                                               OCO     H               H   H  NOCH.sub.3                                   141                                                                               COCH.sub.2                                                                             H               H   H  NOCH.sub.3                                   142                                                                               COCH.sub.2                                                                             CH.sub.3        H   H  NOCH.sub.3                                   143                                                                               COCH.sub.2                                                                             C.sub.6 H.sub.5 H   H  NOCH.sub.3                                   144                                                                               COCH.sub.2                                                                             2-CH.sub.3C.sub.6 H.sub.4                                                                      H   H  NOCH.sub.3                                   145                                                                               COCH.sub.2                                                                             2,4-(CH.sub.3).sub.2 C.sub.6 H.sub.3                                                           H   H  NOCH.sub.3                                   146                                                                               COCH.sub.2                                                                             2-ClC.sub.6 H.sub.4                                                                            H   H  NOCH.sub.3                                   147                                                                               CH.sub.2CO                                                                             H               H   H  NOCH.sub.3                                   148                                                                               CH.sub.2CO                                                                             C.sub.6 H.sub.5 H   H  NOCH.sub.3                                   149                                                                               NN      C.sub.6 H.sub.5 H   H  NOCH.sub.3                                   150                                                                               CH.sub.2                                                                               H               CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   150                                                                               CH.sub.2                                                                               H               CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   151                                                                               CHCl    H               CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   152                                                                               CHBr    H               CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   153                                                                               CHI     H               CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   154                                                                               CH.sub.2CH.sub.2                                                                       C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   155                                                                               CH.sub.2CH.sub.2                                                                       2-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   156                                                                               CH.sub. 2CH.sub.2                                                                      3-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   157                                                                               CH.sub.2CH.sub.2                                                                       4-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   158                                                                               CH.sub.2CH.sub.2                                                                       2-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   159                                                                               CH.sub.2CH.sub.2                                                                       3-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   160                                                                               CH.sub.2CH.sub.2                                                                       4-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   161                                                                               CH.sub.2CH.sub.2                                                                       2-BrC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   162                                                                               CH.sub.2CH.sub.2                                                                       4-BrC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   163                                                                               CH.sub.2CH.sub.2                                                                       2-IC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   164                                                                               CH.sub.2CH.sub.2                                                                       2-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   165                                                                               CH.sub.2CH.sub.2                                                                       3-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   166                                                                               CH.sub.2CH.sub.2                                                                       4-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   167                                                                               CH.sub.2CH.sub.2                                                                       2-OCH.sub.3C.sub.6 H.sub.4                                                                     CH.sub. 3                                                                          CH.sub.3                                                                          NOCH.sub.3                                   168                                                                               CH.sub.2CH.sub.2                                                                       3-OCH.sub.3C.sub.6 H.sub.4                                                                     CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   169                                                                               CH.sub.2CH.sub.2                                                                       4-OCH.sub.3C.sub.6 H.sub.4                                                                     CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   170                                                                               CH.sub.2CH.sub.2                                                                       2-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   171                                                                               CH.sub.2CH.sub.2                                                                       3-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   172                                                                               CH.sub.2CH.sub.2                                                                       4-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   173                                                                               CH.sub.2CH.sub.2                                                                       2,4-Cl.sub.2C.sub.6 H.sub.3                                                                    CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   174                                                                               CH.sub.2CH.sub.2                                                                       2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   175                                                                               CH.sub.2CH.sub.2                                                                       2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2                                                          CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   176                                                                               CH.sub.2CH.sub.2                                                                       Pyridin-3-yl    CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   177                                                                               CH.sub.2CH.sub.2                                                                       Furan-2-yl      CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   178                                                                               CH.sub.2CH.sub.2                                                                       6-CH.sub.3 -Pyridin-2-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   179                                                                               CH.sub.2CH.sub.2                                                                       Benzothiazol-2-yl                                                                              CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   180                                                                               CHCH    C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   181                                                                               CHCH    2-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   182                                                                               CHCH    3-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   183                                                                               CHCH    4-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   184                                                                               CHCH    2-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   185                                                                               CHCH    3-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   186                                                                               CHCH    4-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   187                                                                               CHCH    2-BrC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   188                                                                               CHCH    4-BrC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   189                                                                               CHCH    2-IC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   190                                                                               CHCH    2-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   191                                                                               CHCH    3-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   192                                                                               CHCH    4-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   193                                                                               CHCH    2-OCH.sub.3C.sub.6 H.sub.4                                                                     CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   194                                                                               CHCH    3-OCH.sub.3C.sub.6 H.sub.4                                                                     CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   195                                                                               CHCH    4-OCH.sub.3C.sub.6 H.sub.4                                                                     CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   196                                                                               CHCH    2-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   197                                                                               CHCH    3-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   198                                                                               CHCH    4-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   199                                                                               CHCH    2,4-Cl.sub.2C.sub.6 H.sub.3                                                                    CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   200                                                                               CHCH    2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   201                                                                               CHCH    2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2                                                          CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   202                                                                               CHCH    Pyridin-3-yl    CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   203                                                                               CHCH    Furan-2-yl      CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   204                                                                               CHCH    6-CH.sub.3 -Pyridin-2-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   205                                                                               CHCH    Benzothiazol-2-yl                                                                              CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   206                                                                               CH.sub.2 O                                                                             C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   207                                                                               CH.sub.2 O                                                                             2-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   208                                                                               CH.sub.2 O                                                                             3-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   209                                                                               CH.sub.2 O                                                                             4-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   210                                                                               CH.sub.2 O                                                                             2-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   211                                                                               CH.sub.2 O                                                                             3-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   212                                                                               CH.sub.2 O                                                                             4-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   213                                                                               CH.sub.2 O                                                                             2-BrC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   214                                                                               CH.sub.2 O                                                                             4-BrC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   215                                                                               CH.sub.2 O                                                                             2-IC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   216                                                                               CH.sub.2 O                                                                             2-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   217                                                                               CH.sub.2 O                                                                             3-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   218                                                                               CH.sub.2 O                                                                             4-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   219                                                                               CH.sub.2 O                                                                             2-OCH.sub.3C.sub.6 H.sub.4                                                                     CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   220                                                                               CH.sub.2 O                                                                             3-OCH.sub.3C.sub.6 H.sub.4                                                                     CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   221                                                                               CH.sub.2 O                                                                             4-OCH.sub.3C.sub.6 H.sub.4                                                                     CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   222                                                                               CH.sub.2 O                                                                             2-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   223                                                                               CH.sub.2 O                                                                             3-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   224                                                                               CH.sub.2 O                                                                             4-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   225                                                                               CH.sub.2 O                                                                             2,4-Cl.sub.2C.sub.6 H.sub.3                                                                    CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   226                                                                               CH.sub.2 O                                                                             2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   227                                                                               CH.sub.2 O                                                                             2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2                                                          CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   228                                                                               CH.sub.2 O                                                                             Pyridin-3-yl    CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   229                                                                               CH.sub.2 O                                                                             Furan-2-yl      CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   230                                                                               CH.sub.2 O                                                                             6-CH.sub.3 -Pyridin-2-yl                                                                       CH.sub.3                                                                           CH.sub. 3                                                                         NOCH.sub.3                                   231                                                                               CH.sub.2 O                                                                             Benzothiazol-2-yl                                                                              CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   232                                                                               OCH.sub.2                                                                              C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   233                                                                               OCH.sub.2                                                                              2-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   234                                                                               OCH.sub.2                                                                              3-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   235                                                                               OCH.sub.2                                                                              4-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   236                                                                               OCH.sub.2                                                                              2-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   237                                                                               OCH.sub.2                                                                              3-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   238                                                                               OCH.sub.2                                                                              4-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   239                                                                               OCH.sub.2                                                                              2-BrC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   240                                                                               OCH.sub.2                                                                              4-BrC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   241                                                                               OCH.sub.2                                                                              2-IC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   242                                                                               OCH.sub.2                                                                              2-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                                                            M.p.75° C.,                                                             1H-NMR(CDCl.sub.3)                                                             2.26(s,3H);3.02,                                                               3,17(2s,6H);3.97(s,3H);5.17(s,2H)                                              ;6.85                                                                          (m,2H);7.15(m,2H);7.40(m,3H);7.60                                              (d,1H)                                243                                                                               OCH.sub.2                                                                              3-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   244                                                                               OCH.sub.2                                                                              4-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   245                                                                               OCH.sub.2                                                                              2-OCH.sub.3C.sub.6 H.sub.4                                                                     CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   246                                                                               OCH.sub.2                                                                              3-OCH.sub.3C.sub.6 H.sub.4                                                                     CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   247                                                                               OCH.sub.2                                                                              4-OCH.sub.3C.sub.6 H.sub.4                                                                     CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   248                                                                               OCH.sub.2                                                                              2-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   249                                                                               OCH.sub.2                                                                              3-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   250                                                                               OCH.sub.2                                                                              4-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   251                                                                               OCH.sub.2                                                                              2,4-Cl.sub.2C.sub.6 H.sub.3                                                                    CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   252                                                                               OCH.sub.2                                                                              2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                                                            oil;1H-NMR(CDCl.sub.3):                                                        δ=2.23(s,3H);2.27                                                        (s,3H);3.03,3.182s,6H);3.93(s,3H)                                              ;5.902(s,2H);                                                                  6.75(d,1H);6.9(m,2H);7.35(m,3H);7                                              .57(d,1H)                             253                                                                               OCH.sub.2                                                                              2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2                                                          CH.sub.3                                                                           CH.sub.3                                                                          N OCH.sub.3                                  254                                                                               OCH.sub.2                                                                              2-CH.sub.3, 4-ClC.sub.6 H.sub.3                                                                CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   255                                                                               OCH.sub.2                                                                              3-t-C.sub.4 H.sub.9C.sub.6 H.sub.4                                                             CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   256                                                                               OCH.sub.2                                                                              2-Cl, 4-CH.sub.3C.sub.6 H.sub.4                                                                CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   257                                                                               OCH.sub.2                                                                              4-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                               CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   258                                                                               OCH.sub.2                                                                              Pyridin-2-yl    CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   259                                                                               OCH.sub.2                                                                              6-CH.sub.3 -Pyridin-2-yl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   260                                                                               OCH.sub.2                                                                              6-Cl-Pyridin-2-yl                                                                              CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   261                                                                               OCH.sub.2                                                                              Benzothiazol-2-yl                                                                              CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   262                                                                               O       H               CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   263                                                                               O       C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   264                                                                               O       3-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                               CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   265                                                                               O       3-n-C.sub.3 H.sub.7OC.sub.6 H.sub.4                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   266                                                                               O       Pyridin-2-yl    CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   267                                                                               O       6-C.sub.6 H.sub.5 -Pyridin-2-yl                                                                CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub. 3                                  268                                                                               O       CH.sub.2CHCH.sub.2                                                                             CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   269                                                                               O       3-C.sub.6 H.sub.5 OC.sub.6 H.sub.4                                                             CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   270                                                                               O       3-C.sub.6 H.sub.5 SC.sub.6 H.sub.4                                                             CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   271                                                                               O       3-C.sub.6 H.sub.5 CH.sub.2 OC.sub.6 H.sub.4                                                    CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   272                                                                               CC      CH.sub.3        CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   273                                                                               CC      C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   274                                                                               S       C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   275                                                                               S       2-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   276                                                                               SCH.sub.2                                                                              C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   277                                                                               SCH.sub.2                                                                              4-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   278                                                                               SCH.sub.2                                                                              4-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   279                                                                               SCH.sub.2                                                                              2-CH.sub.3 -Pyridin-2-yl                                                                       CH.sub. 3                                                                          CH.sub.3                                                                          NOCH.sub.3                                   280                                                                               SCH.sub.2                                                                              6-Cl-Pyridin-2-yl                                                                              CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   281                                                                               SCH.sub.2                                                                              Benzothiazol-2-yl                                                                              CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   282                                                                               SCH.sub.2                                                                              5-Cl-Benzothiazol-2-yl                                                                         CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   283                                                                               SCH.sub.2                                                                              6-Cl-Benzothiazol-2-yl                                                                         CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   284                                                                               COO     CH.sub.3        CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   285                                                                               COO     C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   286                                                                               OCO     CH.sub.3        CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   287                                                                               OCO     C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   288                                                                               OCO     H               CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   289                                                                               COCH.sub.2                                                                             H               CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   290                                                                               COCH.sub.2                                                                             CH.sub.3        CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   291                                                                               COCH.sub.2                                                                             C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   292                                                                               COCH.sub.2                                                                             2-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   293                                                                               COCH.sub.2                                                                             2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   294                                                                               CO CH.sub.2                                                                            2-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   295                                                                               COCH.sub.2                                                                             Pyridin-2-yl    CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   296                                                                               COCH.sub.2                                                                             Furan-2-yl      CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   297                                                                               COCH.sub.2                                                                             Benzothiazol-2-yl                                                                              CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   298                                                                               CH.sub.2CO                                                                             H               CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   299                                                                               CH.sub.2CO                                                                             C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   200                                                                               NN      C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   301                                                                               COOCH.sub.2                                                                            CH.sub.3        CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.2                                   302                                                                               COOCH.sub.2                                                                            tert.-C.sub.4 H.sub.9                                                                          CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.2                                   303                                                                               COOCH.sub.2                                                                            3-Heptyl        CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.2                                   304                                                                               COOCH.sub.2                                                                            Cyclopropyl     CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.2                                   305                                                                               COOCH.sub.2                                                                            1-Methylcyclopropyl                                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.2                                   306                                                                               COOCH.sub.2                                                                            2-Methylcyclopropyl                                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.2                                   307                                                                               COOCH.sub.2                                                                            2,2-Dimethylcycloproppyl                                                                       CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.2                                   308                                                                               COOCH.sub.2                                                                            2,2-Dichlorocyclopropyl                                                                        CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.2                                   309                                                                               COOCH.sub.2                                                                            2,2-Dimethyl-3-(2,2-Dichloro-                                                                  CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.2                                              vinyl)cyclopropyl                                                   310                                                                               COOCH.sub.2                                                                            2-Phenylcyclopropyl                                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.2                                   311                                                                               COOCH.sub.2                                                                            1-(2-Fluorophenyl)cyclopropyl                                                                  CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.2                                   312                                                                               COOCH.sub.2                                                                            1-(2-Chlorophenyl)cyclopropyl                                                                  CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.2                                   313                                                                               COOCH.sub.2                                                                            1-(2,6-Difluorophenyl)-                                                                        CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.2                                              cyclopropyl                                                         314                                                                               COOCH.sub.2                                                                            1-(2,4-Dichlorophenyl)-                                                                        CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.2                                              cyclopropyl                                                         315                                                                               COOCH.sub.2                                                                            1-(4-Chlorophenyl)cyclopropyl                                                                  CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.2                                   316                                                                               COOCH.sub.2                                                                            1-(4-Methoxyphenyl)-cyclopropyl                                                                CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.2                                   317                                                                               COOCH.sub.2                                                                            1-(2-Methylphenyl)cyclopropyl                                                                  CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.2                                   318                                                                               COOCH.sub.2                                                                            1-(4-Methylphenyl)cyclopropyl                                                                  CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.2                                   319                                                                               COOCH.sub.2                                                                            1-Benzylcyclopropyl                                                                            CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.2                                   320                                                                               COOCH.sub.2                                                                            Phenyl          CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.2                                   321                                                                               COOCH.sub.2                                                                            4-Methylphenyl  CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.2                                   322                                                                               COOCH.sub.2                                                                            4-Chlorophenyl  CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.2                                   323                                                                               COOCH.sub.2                                                                            4-Fluorophenyl  CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.2                                   324                                                                               COOCH.sub.2                                                                            2-Heptyl        CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   325                                                                               COOCH.sub.2                                                                            Propargyl       CH.sub.3                                                                           CH.sub. 3                                                                         NOCH.sub.3                                   326                                                                               COOCH.sub.2                                                                            1-Methylcyclohexyl                                                                             CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   327                                                                               COOCH.sub.2                                                                            Cyclohexyl      CH.sub.3                                                                           CH.sub.3                                                                          NOCH.sub.3                                   328                                                                               OCH.sub.2                                                                              C.sub.6 H.sub.5 C.sub.2 H.sub.5                                                                    CH.sub.3                                                                          NOCH.sub.3                                   329                                                                               OCH.sub.2                                                                              C.sub.6 H.sub.5 C.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5                                                                   NOCH.sub.3                                   330                                                                               OCH.sub.2                                                                              C.sub.6 H.sub.5 n-C.sub.3 H.sub.7                                                                  CH.sub.3                                                                          NOCH.sub.3                                   331                                                                               CH.sub.2                                                                               H               CH.sub.3                                                                           H  NOCH.sub.3                                   332                                                                               CHCl    H               CH.sub.3                                                                           H  NOCH.sub.3                                   333                                                                               CHBr    H               CH.sub.3                                                                           H  NOCH.sub.3                                   334                                                                               CHO     H               CH.sub.3                                                                           H  NOCH.sub.3                                   335                                                                               CH.sub.2 O                                                                             H               CH.sub.3                                                                           H  NOCH.sub.3                                   336                                                                               CH.sub.2OSO.sub.2                                                                      CH.sub.3        CH.sub.3                                                                           H  NOCH.sub.3                                   337                                                                               CH.sub.2OSO.sub.2                                                                      C.sub.6 H.sub.4CH.sub.3                                                                        CH.sub.3                                                                           H  NOCH.sub.3                                   338                                                                               CH.sub.2 CH.sub.2                                                                      C.sub.6 H.sub.5 CH.sub.3                                                                           H  NOCH.sub.3                                   339                                                                               CH.sub.2 CH.sub.2                                                                      2-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           H  NOCH.sub.3                                   340                                                                               CH.sub.2 CH.sub.2                                                                      3-FC.sub.6 H.sub.4                                                                             CH.sub. 3                                                                          H  NOCH.sub.3                                   341                                                                               CH.sub.2 CH.sub.2                                                                      4-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           H  NOCH.sub.3                                   342                                                                               CH.sub.2 CH.sub.2                                                                      2-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   343                                                                               CH.sub.2 CH.sub.2                                                                      3-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   344                                                                               CH.sub.2 CH.sub.2                                                                      4-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   345                                                                               CH.sub.2 CH.sub.2                                                                      2-BrC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   346                                                                               CH.sub.2 CH.sub.2                                                                      3-BrC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   347                                                                               CH.sub.2 CH.sub.2                                                                      4-BrC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   348                                                                               CH.sub.2 CH.sub.2                                                                      2-IC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           H  NOCH.sub.3                                   349                                                                               CH.sub.2 CH.sub.2                                                                      2-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  NOCH.sub.3                                   350                                                                               CH.sub.2 CH.sub.2                                                                      3-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  NOCH.sub.3                                   351                                                                               CH.sub.2 CH.sub.2                                                                      4-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  NOCH.sub.3                                   352                                                                               CH.sub.2 CH.sub.2                                                                      2-OCH.sub.3C.sub.64                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   353                                                                               CH.sub.2 CH.sub.2                                                                      3-OCH.sub.3C.sub.6 H.sub.4                                                                     CH.sub.3                                                                           H  NOCH.sub.3                                   354                                                                               CH.sub.2 CH.sub.2                                                                      4-OCH.sub.3C.sub.6 H.sub.4                                                                     CH.sub.3                                                                           H  NOCH.sub.3                                   355                                                                               CH.sub.2 CH.sub.2                                                                      2-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  NOCH.sub.3                                   356                                                                               CH.sub.2 CH.sub.2                                                                      3-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  NOCH.sub.3                                   357                                                                               CH.sub.2 CH.sub.2                                                                      4-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  NOCH.sub.3                                   358                                                                               CH.sub.2 CH.sub.2                                                                      4-i-C.sub.3 H.sub.7C.sub.4 H.sub.9                                                             CH.sub.3                                                                           H  NOCH.sub.3                                   359                                                                               CH.sub.2 CH.sub.2                                                                      4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4                                                             CH.sub.3                                                                           H  NOCH.sub.3                                   360                                                                               CH.sub.2 CH.sub.2                                                                      4-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                               CH.sub.3                                                                           H  NOCH.sub.3                                   361                                                                               CH.sub.2 CH.sub.2                                                                      2,4-Cl.sub.2C.sub.6 H.sub.3                                                                    CH.sub.3                                                                           H  NOCH.sub.3                                   362                                                                               CH.sub.2 CH.sub.2                                                                      2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   363                                                                               CH.sub.2 CH.sub.2                                                                      2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2                                                          CH.sub.3                                                                           H  NOCH.sub.3                                   364                                                                               CH.sub.2 CH.sub. 2                                                                     2,4,6-Cl.sub.3C.sub.6 H.sub.2                                                                  CH.sub.3                                                                           H  NOCH.sub.3                                   365                                                                               CH.sub.2 CH.sub.2                                                                      Pyridin-2-yl    CH.sub.3                                                                           H  NOCH.sub.3                                   366                                                                               CH.sub.2 CH.sub.2                                                                      Pyridin-3-yl    CH.sub.3                                                                           H  NOCH.sub.3                                   367                                                                               CH.sub.2 CH.sub.2                                                                      Furan-2-yl      CH.sub.3                                                                           H  NOCH.sub.3                                   368                                                                               CH.sub.2 CH.sub.2                                                                      6-CH.sub.3 -Pyridin-2-yl                                                                       CH.sub.3                                                                           H  NOCH.sub.3                                   369                                                                               CH.sub.2 CH.sub.2                                                                      6-Cl-Pyridin-2-yl                                                                              CH.sub.3                                                                           H  NOCH.sub.3                                   370                                                                               CH.sub.2 CH.sub.2                                                                      Benzothiazol-2-yl                                                                              CH.sub.3                                                                           H  NOCH.sub.3                                   371                                                                               CHCH    C.sub.6 H.sub.5 CH.sub.3                                                                           H  NOCH.sub.3                                   372                                                                               CHCH    2-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           H  NOCH.sub.3                                   373                                                                               CHCH    3-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           H  NOCH.sub.3                                   374                                                                               CHCH    4-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           H  NOCH.sub.3                                   375                                                                               CHCH    2-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   376                                                                               CHCH    3-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   377                                                                               CHCH    4-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   378                                                                               CHCH    2-BrC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   379                                                                               CH CH   3-BrC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   380                                                                               CHCH    4-BrC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   381                                                                               CHCH    2-IC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           H  NOCH.sub.3                                   382                                                                               CHCH    2-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  NOCH.sub.3                                   383                                                                               CHCH    3-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  NOCH.sub.3                                   384                                                                               CHCH    4-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  NOCH.sub.3                                   385                                                                               CHCH    2-OCH.sub.3C.sub.64                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   386                                                                               CHCH    3-OCH.sub.3C.sub.6 H.sub.4                                                                     CH.sub.3                                                                           H  NOCH.sub.3                                   387                                                                               CHCH    4-OCH.sub.3C.sub.6 H.sub.4                                                                     CH.sub.3                                                                           H  NOCH.sub.3                                   388                                                                               CHCH    2-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  NOCH.sub.3                                   389                                                                               CHCH    3-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  NOCH.sub.3                                   390                                                                               CHCH    4-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  NOCH.sub.3                                   391                                                                               CHCH    4-i-C.sub.3 H.sub.7C.sub.6 H.sub.4                                                             CH.sub.3                                                                           H  NOCH.sub.3                                   392                                                                               CHCH    4-t-C.sub.4 H.sub.9C.sub.6 H.sub. 4                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   393                                                                               CHCH    4-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                               CH.sub.3                                                                           H  NOCH.sub.3                                   394                                                                               CHCH    2,4-Cl.sub.2C.sub.6 H.sub.3                                                                    CH.sub.3                                                                           H  NOCH.sub.3                                   395                                                                               CHCH    2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   396                                                                               CHCH    2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2                                                          CH.sub.3                                                                           H  NOCH.sub.3                                   397                                                                               CHCH    2,4,6-Cl.sub.3C.sub.6 H.sub.2                                                                  CH.sub.3                                                                           H  NOCH.sub.3                                   398                                                                               CHCH    Pyridin-2-yl    CH.sub.3                                                                           H  NOCH.sub.3                                   399                                                                               CHCH    Pyridin-3-yl    CH.sub.3                                                                           H  NOCH.sub.3                                   400                                                                               CHCH    Furan-2-yl      CH.sub.3                                                                           H  NOCH.sub.3                                   401                                                                               CHCH    6-CH.sub.3 -Pyridin-2-yl                                                                       CH.sub.3                                                                           H  NOCH.sub.3                                   402                                                                               CHCH    6-Cl-Pyridin-2-yl                                                                              CH.sub.3                                                                           H  NOCH.sub.3                                   403                                                                               CHCH    Benzothiazol-2-yl                                                                              CH.sub.3                                                                           H  NOCH.sub.3                                   404                                                                               CH.sub.2 O                                                                             C.sub.6 H.sub.5 CH.sub.3                                                                           H  NOCH.sub.3                                   405                                                                               CH.sub.2 O                                                                             2-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           H  NOCH.sub.3                                   406                                                                               CH.sub.2 O                                                                             3-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           H  NOCH.sub.3                                   407                                                                               CH.sub.2 O                                                                             4-FC.sub. 6 H.sub.4                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   408                                                                               CH.sub.2 O                                                                             2-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   409                                                                               CH.sub.2 O                                                                             3-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   410                                                                               CH.sub.2 O                                                                             4-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   411                                                                               CH.sub.2 O                                                                             2-BrC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   412                                                                               CH.sub.2 O                                                                             3-BrC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   413                                                                               CH.sub.2 O                                                                             4-BrC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   414                                                                               CH.sub.2 O                                                                             2-IC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           H  NOCH.sub.3                                   415                                                                               CH.sub.2 O                                                                             2-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  NOCH.sub.3                                   416                                                                               CH.sub.2 O                                                                             3-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  NOCH.sub.3                                   417                                                                               CH.sub.2 O                                                                             4-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  NOCH.sub.3                                   418                                                                               CH.sub.2 O                                                                             2-OCH.sub.3C.sub.64                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   419                                                                               CH.sub.2 O                                                                             3-OCH.sub.3C.sub.6 H.sub.4                                                                     CH.sub.3                                                                           H  NOCH.sub.3                                   420                                                                               CH.sub.2 O                                                                             4-OCH.sub.3C.sub.6 H.sub.4                                                                     CH.sub.3                                                                           H  NOCH.sub.3                                   421                                                                               CH.sub.2 O                                                                             2-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  NOCH.sub.3                                   422                                                                               CH.sub.2 O                                                                             3-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  NOCH.sub.3                                   423                                                                               CH.sub.2 O                                                                             4-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  NOCH.sub.3                                   424                                                                               CH.sub.2 O                                                                             4-i-C.sub.3 H.sub.7C.sub.6 H.sub.4                                                             CH.sub.3                                                                           H  NOCH.sub.3                                   425                                                                               CH.sub.2 O                                                                             4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4                                                             CH.sub.3                                                                           H  NOCH.sub.3                                   426                                                                               CH.sub.2 O                                                                             4-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                               CH.sub.3                                                                           H  NOCH.sub.3                                   427                                                                               CH.sub.2 O                                                                             2,4-Cl.sub.2C.sub.6 H.sub.3                                                                    CH.sub.3                                                                           H  NOCH.sub.3                                   428                                                                               CH.sub.2 O                                                                             2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   429                                                                               CH.sub.2 O                                                                             2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2                                                          CH.sub.3                                                                           H  NOCH.sub.3                                   430                                                                               CH.sub.2 O                                                                             2,4,6-Cl.sub.3C.sub.6 H.sub.2                                                                  CH.sub.3                                                                           H  NOCH.sub.3                                   431                                                                               CH.sub.2 O                                                                             Pyridin-2-yl    CH.sub.3                                                                           H  NOCH.sub.3                                   432                                                                               CH.sub.2 O                                                                             Pyridin-3-yl    CH.sub.3                                                                           H  NOCH.sub.3                                   433                                                                               CH.sub.2 O                                                                             Furan-2-yl      CH.sub.3                                                                           H  NOCH.sub.3                                   434                                                                               CH.sub.2 O                                                                             6-CH.sub.3 -Pyridin-2-yl                                                                       CH.sub.3                                                                           H  NOCH.sub.3                                   435                                                                               CH.sub.2 O                                                                             6-Cl-Pyridin-2-yl                                                                              CH.sub.3                                                                           H  NOCH.sub.3                                   436                                                                               CH.sub.2 O                                                                             Benzothiazol-2-yl                                                                              CH.sub.2                                                                           H  NOCH.sub.3                                   437                                                                               OCH.sub.2                                                                              H               CH.sub.3                                                                           H  NOCH.sub.3                                   438                                                                               OCH.sub.2                                                                              C.sub.6 H.sub.5 CH.sub.3                                                                           H  NOCH.sub.3                                   439                                                                               OCH.sub.2                                                                              2-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           H  NOCH.sub.3                                   440                                                                               OCH.sub.2                                                                              3-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           H  NOCH.sub.3                                   441                                                                               OCH.sub.2                                                                              4-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           H  NOCH.sub.3                                   442                                                                               OCH.sub.2                                                                              2-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   443                                                                               OCH.sub.2                                                                              3-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   444                                                                               OCH.sub.2                                                                              4-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   445                                                                               OCH.sub.2                                                                              2-BrC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   446                                                                               OCH.sub.2                                                                              3-BrC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   447                                                                               OCH.sub.2                                                                              4-BrC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   448                                                                               OCH.sub.2                                                                              2-IC.sub. 6 H.sub.4                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   449                                                                               OCH.sub.2                                                                              2-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  NOCH.sub.3                                                                            M.p.105° C.;1H-NMR(CDCl.su                                              b.3): δ=2.22(s,3H);2.85(d,                                               3H);3.85(s,3H);4.95(s,2H);6.70(sb                                              r,1H);6.80                                                                     (mc,2H);7.0-7.5(m,6H)                 450                                                                               OCH.sub.2                                                                              3-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  NOCH.sub.3                                   451                                                                               OCH.sub.2                                                                              4-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  NOCH.sub.3                                   452                                                                               OCH.sub.2                                                                              2-OCH.sub.3C.sub.64                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   453                                                                               OCH.sub.2                                                                              3-OCH.sub.3C.sub.6 H.sub.4                                                                     CH.sub.3                                                                           H  NOCH.sub.3                                   454                                                                               OCH.sub.2                                                                              4-OCH.sub.3C.sub.6 H.sub.4                                                                     CH.sub.3                                                                           H  NOCH.sub.3                                   455                                                                               OCH.sub.2                                                                              2-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  NOCH.sub.3                                   456                                                                               OCH.sub.2                                                                              3-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  NOCH.sub.3                                   457                                                                               OCH.sub.2                                                                              4-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  NOCH.sub.3                                   458                                                                               OCH.sub.2                                                                              2-NO.sub.2C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  NOCH.sub.3                                   459                                                                               OCH.sub.2                                                                              4-NO.sub.2C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  NOCH.sub.3                                   460                                                                               OCH.sub.2                                                                              2-CH.sub.2 ClC.sub.6 H.sub.4                                                                   CH.sub.3                                                                           H  NOCH.sub.3                                   461                                                                               OCH.sub.2                                                                              3-CH.sub.2 ClC.sub.6 H.sub.4                                                                   CH.sub.3                                                                           H  NOCH.sub.3                                   462                                                                               OCH.sub.2                                                                              4-CH.sub.2 ClC.sub.6 H.sub.4                                                                   CH.sub.3                                                                           H  NOCH.sub.3                                   463                                                                               OCH.sub.2                                                                              2-C.sub.2 H.sub.5C.sub.6 H.sub.4                                                               CH.sub.3                                                                           H  NOCH.sub.3                                   464                                                                               OCH.sub.2                                                                              3-C.sub.2 H.sub.5C.sub.6 H.sub.4                                                               CH.sub.3                                                                           H  NOCH.sub.3                                   465                                                                               OCH.sub.2                                                                              4-C.sub.2 H.sub.5C.sub.6 H.sub.4                                                               CH.sub.3                                                                           H  NOCH.sub.3                                   466                                                                               OCH.sub.2                                                                              3-i-C.sub.3 H.sub.7C.sub.6 H.sub.4                                                             CH.sub.3                                                                           H  NOCH.sub.3                                   467                                                                               OCH.sub.2                                                                              4-i-C.sub.3 H.sub.7C.sub.6 H.sub.4                                                             CH.sub.3                                                                           H  NOCH.sub.3                                   468                                                                               OCH.sub.2                                                                              3-t-C.sub.4 H.sub.9C.sub.6 H.sub.4                                                             CH.sub.3                                                                           H  NOCH.sub.3                                   469                                                                               OCH.sub.2                                                                              4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4                                                             CH.sub.3                                                                           H  NOCH.sub.3                                   470                                                                               OCH.sub.2                                                                              3-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                               CH.sub.3                                                                           H  NOCH.sub.3                                   471                                                                               OCH.sub.2                                                                              4-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                               CH.sub.3                                                                           H  NOCH.sub.3                                   472                                                                               OCH.sub.2                                                                              4-i-C.sub. 3 H.sub.7 OC.sub.6 H.sub.4                                                          CH.sub.3                                                                           H  NOCH.sub.3                                   473                                                                               OCH.sub.2                                                                              4-t-C.sub.4 H.sub.9 OC.sub.6 H.sub.4                                                           CH.sub.3                                                                           H  NOCH.sub.3                                   474                                                                               OCH.sub.2                                                                              3-C.sub.6 H.sub.5 OC.sub.6 H.sub.4                                                             CH.sub.3                                                                           H  NOCH.sub.3                                   475                                                                               OCH.sub.2                                                                              4-C.sub.6 H.sub.5 OC.sub.6 H.sub.4                                                             CH.sub.3                                                                           H  NOCH.sub.3                                   476                                                                               OCH.sub.2                                                                              3-C.sub.6 H.sub.5 CH.sub.2 OC.sub.6 H.sub.4                                                    CH.sub.3                                                                           H  NOCH.sub.3                                   477                                                                               OCH.sub.2                                                                              4-C.sub.6 H.sub.5 CH.sub.2 OC.sub.6 H.sub.4                                                    CH.sub.3                                                                           H  NOCH.sub.3                                   478                                                                               OCH.sub.2                                                                              2,3-Cl.sub.2C.sub.6 H.sub.3                                                                    CH.sub.3                                                                           H  NOCH.sub.3                                   479                                                                               OCH.sub.2                                                                              2,4-Cl.sub.2C.sub.6 H.sub.3                                                                    CH.sub.3                                                                           H  NOCH.sub.3                                   480                                                                               OCH.sub.2                                                                              2,5-Cl.sub.2C.sub.6 H.sub.3                                                                    CH.sub.3                                                                           H  NOCH.sub.3                                   481                                                                               OCH.sub.2                                                                              2,6-Cl.sub.2C.sub.6 H.sub.3                                                                    CH.sub.3                                                                           H  NOCH.sub.3                                   482                                                                               OCH.sub.2                                                                              2,3,4-Cl.sub.3C.sub.6 H.sub.2                                                                  CH.sub.3                                                                           H  NOCH.sub.3                                   483                                                                               OCH.sub.2                                                                              2,3,5-Cl.sub.3C.sub.6 H.sub.4                                                                  CH.sub.3                                                                           H  NOCH.sub.3                                   484                                                                               OCH.sub. 2                                                                             2,3,6-Cl.sub.3C.sub.6 H.sub.2                                                                  CH.sub.3                                                                           H  NOCH.sub.3                                   485                                                                               OCH.sub.2                                                                              3,4,5-Cl.sub.3C.sub.6 H.sub.2                                                                  CH.sub.3                                                                           H  NOCH.sub.3                                   486                                                                               OCH.sub.2                                                                              C.sub.6 Cl.sub.5                                                                               CH.sub.3                                                                           H  NOCH.sub.3                                   487                                                                               OCH.sub.2                                                                              C.sub.6 F.sub.5 CH.sub.3                                                                           H  NOCH.sub.3                                   488                                                                               OCH.sub.2                                                                              2-F, 4-ClC.sub.6 H.sub.3                                                                       CH.sub.3                                                                           H  NOCH.sub.3                                   489                                                                               OCH.sub.2                                                                              4-F, 2-ClC.sub.6 H.sub.3                                                                       CH.sub.3                                                                           H  NOCH.sub.3                                   490                                                                               OCH.sub.2                                                                              2-CH.sub.3, 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.3                                                 CH.sub.3                                                                           H  NOCH.sub.3                                   491                                                                               OCH.sub.2                                                                              2-CH.sub.3, 4-c-C.sub.6 H.sub.11C.sub.6 H.sub.3                                                CH.sub.3                                                                           H  NOCH.sub.3                                   492                                                                               OCH.sub.2                                                                              2-CH.sub.3, 4-C.sub.3 H.sub.7C.sub.6 H.sub.3                                                   CH.sub.3                                                                           H  NOCH.sub.3                                   493                                                                               OCH.sub.2                                                                              2,3-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   494                                                                               OCH.sub.2                                                                              2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                            CH.sub.3                                                                           H  NOCH.sub.3                                                                            M.p.88-89° C.;IR(KBr):                                                  3411,1660,1512,1226,1036,982,798,                                              766                                   495                                                                               OCH.sub.2                                                                              2,5-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   496                                                                               OCH.sub.2                                                                              2,3,5-(CH.sub.3).sub.3C.sub.6 H.sub.2                                                          CH.sub.3                                                                           H  NOCH.sub.3                                   497                                                                               OCH.sub.2                                                                              2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2                                                          CH.sub.3                                                                           H  NOCH.sub.3                                   498                                                                               OCH.sub.2                                                                              3,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   499                                                                               OCH.sub.2                                                                              3,5(CH.sub.3).sub.2C.sub.6 H.sub.3                                                             CH.sub.3                                                                           H  NOCH.sub.3                                   500                                                                               OCH.sub.2                                                                              3,5(C.sub.2 H.sub.5).sub.2C.sub.6 H.sub.3                                                      CH.sub.3                                                                           H  NOCH.sub.3                                   501                                                                               OCH.sub.2                                                                              4-Cyclohexyl-C.sub.6 H.sub.4                                                                   CH.sub.3                                                                           H  NOCH.sub.3                                   502                                                                               OCH.sub.2                                                                              CH.sub.2CHCH.sub.2                                                                             CH.sub.3                                                                           H  NOCH.sub.3                                   503                                                                               OCH.sub.2                                                                              CH.sub.2CHCHCH.sub.3                                                                           CH.sub.3                                                                           H  NOCH.sub.3                                   504                                                                               OCH.sub.2                                                                              CH.sub.2CC(CH.sub.3).sub.2                                                                     CH.sub.3                                                                           H  NOCH.sub.3                                   505                                                                               OCH.sub.2                                                                              CH.sub.2C(CH.sub.3)CH.sub.2                                                                    CH.sub.3                                                                           H  NOCH.sub.3                                   506                                                                               OCH.sub.2                                                                              CH.sub.2C.sub.6 H.sub.5                                                                        CH.sub.3                                                                           H  NOCH.sub.3                                   507                                                                               OCH.sub.2                                                                              Cyclohexyl      CH.sub.3                                                                           H  NOCH.sub.3                                   508                                                                               OCH.sub.2                                                                              CH.sub.2CCH     CH.sub.3                                                                           H  NOCH.sub.3                                   509                                                                               OCH.sub.2                                                                              CH.sub.2 CHCHC.sub.6 H.sub.5                                                                   CH.sub.3                                                                           H  NOCH.sub.3                                   510                                                                               OCH.sub.2                                                                              CH.sub.2 CH.sub.2OC.sub.6 H.sub.5                                                              CH.sub.3                                                                           H  NOCH.sub.3                                   511                                                                               O       H               CH.sub.3                                                                           H  NOCH.sub.3                                   512                                                                               O       C.sub.6 H.sub.5 CH.sub.3                                                                           H  NOCH.sub.3                                   513                                                                               O       3-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                               CH.sub.3                                                                           H  NOCH.sub.3                                   514                                                                               O       3-n-C.sub.3 H.sub.7 OC.sub.6 H.sub.4                                                           CH.sub.3                                                                           H  NOCH.sub.3                                   515                                                                               O       Pyridin-2-yl    CH.sub.3                                                                           H  NOCH.sub.3                                   516                                                                               O       6-C.sub.6 H.sub.5 -Pyridin-2-yl                                                                CH.sub.3                                                                           H  NOCH.sub.3                                   517                                                                               O       CH.sub.2CHCH.sub.2                                                                             CH.sub.3                                                                           H  NOCH.sub.3                                   518                                                                               O       3-C.sub.6 H.sub.5 OC.sub.6 H.sub.4                                                             CH.sub.3                                                                           H  NOCH.sub.3                                   519                                                                               O       3-C.sub.6 H.sub.5SC.sub.6 H.sub.4                                                              CH.sub.3                                                                           H  NOCH.sub.3                                   520                                                                               O       3-C.sub.6 H.sub.5 CH.sub.2 OC.sub.6 H.sub.4                                                    CH.sub.3                                                                           H  NOCH.sub.3                                   521                                                                               O       4-C.sub.6 H.sub.5 OC.sub.6 H.sub.4                                                             CH.sub.3                                                                           H  NOCH.sub.3                                   522                                                                               O       4-C.sub.6 H.sub.5 OCH.sub.2C.sub.6 H.sub.4                                                     CH.sub.3                                                                           H  NOCH.sub.3                                   523                                                                               CC      CH.sub.3        CH.sub.3                                                                           H  NOCH.sub.3                                   524                                                                               CC      C.sub.6 H.sub.5 CH.sub.3                                                                           H  NOCH.sub.3                                   525                                                                               S       C.sub.6 H.sub.5 CH.sub.3                                                                           H  NOCH.sub.3                                   526                                                                               S       2-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   527                                                                               SCH.sub.2                                                                              C.sub.6 H.sub.5 CH.sub.3                                                                           H  NOCH.sub.3                                   528                                                                               SCH.sub.2                                                                              2-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   529                                                                               SCH.sub.2                                                                              4-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   530                                                                               SCH.sub.2                                                                              4-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           H  NOCH.sub.3                                   531                                                                               SCH.sub.2                                                                              4-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  NOCH.sub.3                                   532                                                                               SCH.sub.2                                                                              4-CH.sub.3 -Pyridin-2-yl                                                                       CH.sub.3                                                                           H  NOCH.sub.3                                   533                                                                               SCH.sub.2                                                                              6-Cl-Pyridin-2-yl                                                                              CH.sub.3                                                                           H  NOCH.sub.3                                   534                                                                               SCH.sub.2                                                                              Benzothiazol-2-yl                                                                              CH.sub.3                                                                           H  NOCH.sub.3                                   535                                                                               SCH.sub.2                                                                              5-Cl-Benzothiazol-2-yl                                                                         CH.sub.3                                                                           H  NOCH.sub.3                                   536                                                                               OCH.sub.2                                                                              6-Cl-Benzothiazol-2-yl                                                                         CH.sub.3                                                                           H  NOCH.sub.3                                   537                                                                               OCH.sub.2                                                                              4,8-(CH.sub.3).sub.2 -Chinolin-2-yl                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   538                                                                               COO     CH.sub.3        CH.sub.3                                                                           H  NOCH.sub.3                                   539                                                                               COO     C.sub.6 H.sub.5 CH.sub.3                                                                           H  NOCH.sub.3                                   540                                                                               OCO     CH.sub.3        CH.sub.3                                                                           H  NOCH.sub.3                                   541                                                                               OCO     C.sub.6 H.sub.5 CH.sub.3                                                                           H  NOCH.sub.3                                   542                                                                               OCO     C.sub.6 H.sub.5CH.sub.2                                                                        CH.sub.3                                                                           H  NOCH.sub.3                                   543                                                                               OCO     H               CH.sub.3                                                                           H  NOCH.sub.3                                   544                                                                               COCH.sub.2                                                                             H               CH.sub.3                                                                           H  NOCH.sub.3                                   545                                                                               COCH.sub.2                                                                             CH.sub.3        CH.sub.3                                                                           H  NOCH.sub.3                                   546                                                                               COCH.sub.2                                                                             C.sub.6 H.sub.5 CH.sub.3                                                                           H  NOCH.sub.3                                   547                                                                               COCH.sub.2                                                                             2-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  NOCH.sub.3                                   548                                                                               COCH.sub.2                                                                             2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   549                                                                               COCH.sub.2                                                                             2-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   550                                                                               CH.sub.2CO                                                                             H               CH.sub.3                                                                           H  NOCH.sub.3                                   551                                                                               CH.sub.2CO                                                                             C.sub.6 H.sub.5 CH.sub. 3                                                                          H  NOCH.sub.3                                   552                                                                               NN      C.sub.6 H.sub.5 CH.sub.3                                                                           H  NOCH.sub.3                                   553                                                                               COOCH.sub.2                                                                            CH.sub.3        CH.sub.3                                                                           H  NOCH.sub.3                                   554                                                                               COOCH.sub.2                                                                            tert.-C.sub.4 H.sub.9                                                                          CH.sub.3                                                                           H  NOCH.sub.3                                   555                                                                               COOCH.sub.2                                                                            3-Heptyl        CH.sub.3                                                                           H  NOCH.sub.3                                   556                                                                               COOCH.sub.2                                                                            Cyclopropyl     CH.sub.3                                                                           H  NOCH.sub.3                                   557                                                                               COOCH.sub.2                                                                            1-Methylcyclopropyl                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   558                                                                               COOCH.sub.2                                                                            2-Methylcyclopropyl                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   559                                                                               COOCH.sub.2                                                                            2,2-Dimethylcycloprppyl                                                                        CH.sub.3                                                                           H  NOCH.sub.3                                   560                                                                               COOCH.sub.2                                                                            2,2-Dichlorocyclopropyl                                                                        CH.sub.3                                                                           H  NOCH.sub.3                                   561                                                                               COOCH.sub.2                                                                            2,2-Dimethyl-3-(2,2-Dichloro-                                                                  CH.sub.3                                                                           H  NOCH.sub.3                                              vinyl)cyclopropyl                                                   562                                                                               COOCH.sub.2                                                                            1-Phenylcyclopropyl                                                                            CH.sub.3                                                                           H  NOCH.sub.3                                   563                                                                               COOCH.sub.2                                                                            1-(2-Fluorophenyl)cyclopropyl                                                                  CH.sub.3                                                                           H  NOCH.sub.3                                   564                                                                               COOCH.sub.2                                                                            1-(2-Chlorophenyl)cyclopropyl                                                                  CH.sub.3                                                                           H  NOCH.sub.3                                   565                                                                               COOCH.sub.2                                                                            1-(2,6-Difluorophenyl)-                                                                        CH.sub.3                                                                           H  NOCH.sub.3                                              cyclopropyl                                                         566                                                                               COOCH.sub.2                                                                            1-(2,4-Dichlorophenyl)-                                                                        CH.sub.3                                                                           H  NOCH.sub.3                                              cyclopropyl                                                         567                                                                               COOCH.sub.2                                                                            1-(4-Chlorophenyl)cyclopropyl                                                                  CH.sub.3                                                                           H  NOCH.sub.3                                   568                                                                               COOCH.sub.2                                                                            1-(4-Methoxyphenyl)cyclopropyl                                                                 CH.sub.3                                                                           H  NOCH.sub.3                                   569                                                                               CH.sub.2                                                                               H               C.sub.2 H.sub.5                                                                    H  NOCH.sub.3                                   570                                                                               CHCl    H               C.sub.2 H.sub.5                                                                    H  NOCH.sub.3                                   571                                                                               CHBr    H               C.sub.2 H.sub.5                                                                    H  NOCH.sub.3                                   572                                                                               CH.sub.2 CH.sub.2                                                                      C.sub.6 H.sub.5 C.sub.2 H.sub.5                                                                    H  NOCH.sub.3                                   573                                                                               CHCH    C.sub.6 H.sub.5 C.sub.2 H.sub.5                                                                    H  NOCH.sub.3                                   574                                                                               OCH.sub.2                                                                              C.sub.6 H.sub.5 C.sub.2 H.sub.5                                                                    H  NOCH.sub.3                                   575                                                                               CH.sub.2 O                                                                             C.sub.6 H.sub.5 C.sub.2 H.sub.5                                                                    H  NOCH.sub.3                                   576                                                                               O       C.sub.6 H.sub.5 C.sub.2 H.sub.5                                                                    H  NOCH.sub.3                                   577                                                                               OCH.sub.2                                                                              C.sub.6 H.sub.5 OCH.sub.3                                                                          H  NOCH.sub.3                                   578                                                                               CHCH    C.sub.6 H.sub.5 OCH.sub.3                                                                          H  NOCH.sub.3                                   579                                                                               CH.sub.2                                                                               H               OCH.sub.3                                                                          H  NOCH.sub.3                                   580                                                                               CHCl    H               OCH.sub.3                                                                          H  NOCH.sub.3                                   581                                                                               CHBr    H               OCH.sub.3                                                                          H  NOCH.sub.3                                   582                                                                               CH.sub.2                                                                               H               OCH.sub.3                                                                          CH.sub.3                                                                          NOCH.sub.3                                   583                                                                               OCH.sub.2                                                                              C.sub.6 H.sub.5 OCH.sub.3                                                                          CH.sub.3                                                                          NOCH.sub.3                                   584                                                                               OCH.sub.2                                                                              C.sub.6 H.sub.5 OC.sub.2 H.sub.5                                                                   H  NOCH.sub.3                                   585                                                                               OCH.sub.2                                                                              2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                            OCH.sub.3                                                                          CH.sub.3                                                                          NOCH.sub.3                                                                            oil;1H-NMR(CDCl.sub.3):                                                        δ=2.24,2.28(2s,6H);3.21(s,                                               3H);3.52(br,3H);3.98(s,3H);5.05(s                                              ,2H);6.75                                                                      (d,1H);6.83(m,2H),7.40(mc,3H);7.6                                              4(d,1H)                               586                                                                               OCH.sub.2                                                                              2-CH.sub.3C.sub.6 H.sub.4                                                                      OCH.sub.3                                                                          CH.sub.3                                                                          NOCH.sub.3                                                                            M.p.55° C.;1H-NMR(CDCl.sub                                              .3): δ=2.30(s,3H);3.20,                                                  3.48(2s,6H);3.98(s,3t);5.08(s,2H)                                              ;6.85(t,2H);                                                                   7.10(m,2H);7.40(mc,3H);7.65(d,1H)     587                                                                               OCH.sub.2                                                                              2-CH.sub.3C.sub.6 H.sub.4                                                                      OCH.sub.3                                                                          H  NOCH.sub.3                                                                            M.p.89° C.;1H-NMR(CDCl.sub                                              .3) δ=2.22(s,3H);3.75(s,                                                 3H);3.94(s,3H);4.98(s,2H);6.80(m,                                              2H);7.13(m,                                                                    2H);7.25(d,1H);7.40(mc,2H);7.55(d                                              ,1H);                                                                          9.15(s,1H)                            588                                                                               OCH.sub.2                                                                              2-CH.sub.3C.sub.6 H.sub.4                                                                      C.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5                                                                   NOCH.sub.3                                                                            oil;1H-NMR(CDCl.sub.3)                                                         δ=1.18(t,3H);2.25(s,3H);                                                 3.45(d,3H);3.93(s,3H);5.09(s,2H);                                              6.85(m,2H)                                                                     7.10(mc,2H);7.4(m,3H);7.60(d,1H)      589                                                                               CH.sub.2                                                                               H               CH.sub.3                                                                           H  CHOCH.sub.3                                  590                                                                               CHCl    H               CH.sub.3                                                                           H  CHOCH.sub.3                                  591                                                                               CHBr    H               CH.sub.3                                                                           H  CHOCH.sub.3                                  592                                                                               CHI     H               CH.sub.3                                                                           H  CHOCH.sub.3                                  593                                                                               CH.sub.2                                                                               OH              CH.sub.3                                                                           H  CHOCH.sub.3                                  594                                                                               CH.sub.2OSO.sub.2                                                                      CH.sub.3        CH.sub.3                                                                           H  CHOCH.sub.3                                  595                                                                               CH.sub.2OSO.sub.2                                                                      C.sub.6 H.sub.4CH.sub.3                                                                        CH.sub.3                                                                           H  CHOCH.sub.3                                  596                                                                               CH.sub.2CH.sub.2                                                                       C.sub.6 H.sub.5 CH.sub.3                                                                           H  CHOCH.sub.3                                  597                                                                               CH.sub.2CH.sub.2                                                                       2-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           H  CHOCH.sub.3                                  598                                                                               CH.sub.2CH.sub.2                                                                       3-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           H  CHOCH.sub.3                                  599                                                                               CH.sub.2CH.sub.2                                                                       4-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           H  CHOCH.sub.3                                  600                                                                               CH.sub.2CH.sub.2                                                                       2-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  601                                                                               CH.sub.2CH.sub.2                                                                       3-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  602                                                                               CH.sub.2CH.sub.2                                                                       4-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  603                                                                               CH.sub.2CH.sub.2                                                                       2-BrC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  604                                                                               CH.sub.2CH.sub.2                                                                       3-BrC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  605                                                                               CH.sub.2CH.sub.2                                                                       4-Br C.sub.6 H.sub.4                                                                           CH.sub.3                                                                           H  CHOCH.sub.3                                  606                                                                               CH.sub.2CH.sub.2                                                                       2-I-C.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  607                                                                               CH.sub.2CH.sub.2                                                                       2-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  CHOCH.sub.3                                  608                                                                               CH.sub.2CH.sub.2                                                                       3-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  CHOCH.sub.3                                  609                                                                               CH.sub.2CH.sub.2                                                                       4-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  CHOCH.sub.3                                  610                                                                               CH.sub.2CH.sub.2                                                                       2-OCH.sub.3C.sub.6 H.sub.4                                                                     CH.sub.3                                                                           H  CHOCH.sub.3                                  611                                                                               CH.sub.2CH.sub.2                                                                       3-OCH.sub.3C.sub.6 H.sub.4                                                                     CH.sub.3                                                                           H  CHOCH.sub.3                                  612                                                                               CH.sub.2CH.sub.2                                                                       4-OCH.sub.3C.sub.6 H.sub.4                                                                     CH.sub.3                                                                           H  CHOCH.sub.3                                  613                                                                               CH.sub.2CH.sub.2                                                                       2-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  CHOCH.sub.3                                  614                                                                               CH.sub.2CH.sub.2                                                                       3-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  CHOCH.sub.3                                  615                                                                               CH.sub.2CH.sub.2                                                                       4-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  CHOCH.sub.3                                  616                                                                               CH.sub.2CH.sub.2                                                                       4-i-C.sub.3 H.sub.7C.sub.6 H.sub.4                                                             CH.sub.3                                                                           H  CHOCH.sub.3                                  617                                                                               CH.sub.2 CH.sub.2                                                                      4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4                                                             CH.sub.3                                                                           H  CHOCH.sub.3                                  618                                                                               CH.sub.2CH.sub.2                                                                       4-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                               CH.sub.3                                                                           H  CHOCH.sub.3                                  619                                                                               CH.sub.2CH.sub.2                                                                       2,4-Cl.sub.2C.sub.6 H.sub.3                                                                    CH.sub.3                                                                           H  CHOCH.sub.3                                  620                                                                               CH.sub.2CH.sub.2                                                                       2,4-(CH.sub.3).sub.4C.sub.6 H.sub.3                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  621                                                                               CH.sub.2CH.sub.2                                                                       2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2                                                          CH.sub.3                                                                           H  CHOCH.sub.3                                  622                                                                               CH.sub.2CH.sub.2                                                                       2,4,6-Cl.sub.3C.sub.6 H.sub.2                                                                  CH.sub.3                                                                           H  CHOCH.sub.3                                  623                                                                               CH.sub.2CH.sub.2                                                                       Pyridin-2-yl    CH.sub.3                                                                           H  CHOCH.sub.3                                  624                                                                               CH.sub.2CH.sub.2                                                                       Pyridin-3-yl    CH.sub.3                                                                           H  CHOCH.sub.3                                  625                                                                               CH.sub.2CH.sub.2                                                                       Furan-2-yl      CH.sub.3                                                                           H  CHOCH.sub.3                                  626                                                                               CH.sub.2CH.sub.2                                                                       6-CH.sub.3 -Pyridin-2-yl                                                                       CH.sub.3                                                                           H  CHOCH.sub.3                                  627                                                                               CH.sub.2CH.sub.2                                                                       6-Cl-Pyridin-2-yl                                                                              CH.sub.3                                                                           H  CHOCH.sub.3                                  628                                                                               CH.sub.2CH.sub.2                                                                       Benzothiazol-2-yl                                                                              CH.sub.3                                                                           H  CHOCH.sub.3                                  629                                                                               CHCH    C.sub.6 H.sub.5 CH.sub.3                                                                           H  CHOCH.sub.3                                  630                                                                               CHCH    2-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           H  CHOCH.sub.3                                  631                                                                               CHCH    3-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           H  CHOCH.sub.3                                  632                                                                               CHCH    4-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           H  CHOCH.sub.3                                  633                                                                               CHCH    2-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  634                                                                               CHCH    3-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  635                                                                               CHCH    4-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  636                                                                               CHCH    2-BrC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  637                                                                               CHCH    3-BrC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  638                                                                               CHCH    4-BrC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  639                                                                               CHCH    2-IC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           H  CHOCH.sub.3                                  640                                                                               CHCH    2-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  CHOCH.sub.3                                  641                                                                               CHCH    3-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  CHOCH.sub.3                                  642                                                                               CHCH    4-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  CHOCH.sub.3                                  643                                                                               CHCH    2-OCH.sub.3C.sub.6 H.sub.4                                                                     CH.sub.3                                                                           H  CHOCH.sub.3                                  644                                                                               CHCH    3-OCH.sub.3C.sub. 6 H.sub.4                                                                    CH.sub.3                                                                           H  CHOCH.sub.3                                  645                                                                               CHCH    4-OCH.sub.3C.sub.6 H.sub.4                                                                     CH.sub.3                                                                           H  CHOCH.sub.3                                  646                                                                               CHCH    2-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  CHOCH.sub.3                                  647                                                                               CHCH    3-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  CHOCH.sub.3                                  648                                                                               CHCH    4-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  CHOCH.sub.3                                  649                                                                               CHCH    4-i-C.sub.3 H.sub.7C.sub.6 H.sub.4                                                             CH.sub.3                                                                           H  CHOCH.sub.3                                  650                                                                               CHCH    4-t-C.sub.3 H.sub.7C.sub.6 H.sub.4                                                             CH.sub.3                                                                           H  CHOCH.sub.3                                  651                                                                               CHCH    4-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                               CH.sub.3                                                                           H  CHOCH.sub.3                                  652                                                                               CHCH    2,4-Cl.sub.2C.sub.6 H.sub.3                                                                    CH.sub.3                                                                           H  CHOCH.sub.3                                  653                                                                               CHCH    2,4-(CH.sub.3).sub.4C.sub.6 H.sub.3                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  654                                                                               CHCH    2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2                                                          CH.sub.3                                                                           H  CHOCH.sub.3                                  655                                                                               CHCH    2,4,6-Cl.sub.3C.sub.6 H.sub.2                                                                  CH.sub.3                                                                           H  CHOCH.sub.3                                  656                                                                               CHCH    Pyridin-2-yl    CH.sub.3                                                                           H  CHOCH.sub.3                                  657                                                                               CHCH    Pyridin-3-yl    CH.sub.3                                                                           H  CHOCH.sub.3                                  658                                                                               CHCH    Furan-2-yl      CH.sub.3                                                                           H  CHOCH.sub.3                                  659                                                                               CHCH    6-CH.sub.3 -Pyridin-2-yl                                                                       CH.sub.3                                                                           H  CHOCH.sub.3                                  660                                                                               CHCH    6-Cl-Pyridin-2-yl                                                                              CH.sub.3                                                                           H  CHOCH.sub.3                                  661                                                                               CHCH    Benzothiazol-2-yl                                                                              CH.sub.3                                                                           H  CHOCH.sub.3                                  662                                                                               CH.sub.2 O                                                                             C.sub.6 H.sub.5 CH.sub.3                                                                           H  CHOCH.sub.3                                  663                                                                               CH.sub.2 O                                                                             2-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           H  CHOCH.sub.3                                  664                                                                               CH.sub.2 O                                                                             3-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           H  CHOCH.sub.3                                  665                                                                               CH.sub.2 O                                                                             4-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           H  CHOCH.sub.3                                  666                                                                               CH.sub.2 O                                                                             2-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  667                                                                               CH.sub.2 O                                                                             3-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  668                                                                               CH.sub.2 O                                                                             4-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  669                                                                               CH.sub.2 O                                                                             2-BrC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  670                                                                               CH.sub.2 O                                                                             3-BrC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  671                                                                               CH.sub.2 O                                                                             4-BrC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  672                                                                               CH.sub.2 O                                                                             2-I C.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  673                                                                               CH.sub.2 O                                                                             2-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  CHOCH.sub.3                                  674                                                                               CH.sub.2 O                                                                             3-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  CHOCH.sub.3                                  675                                                                               CH.sub.2 O                                                                             4-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  CHOCH.sub.3                                  676                                                                               CH.sub.2 O                                                                             2-OCH.sub.3C.sub.6 H.sub.4                                                                     CH.sub.3                                                                           H  CHOCH.sub.3                                  677                                                                               CH.sub.2 O                                                                             3-OCH.sub.3C.sub.6 H.sub.4                                                                     CH.sub.3                                                                           H  CHOCH.sub.3                                  678                                                                               CH.sub.2 O                                                                             4-OCH.sub.3C.sub.6 H.sub.4                                                                     CH.sub.3                                                                           H  CHOCH.sub.3                                  679                                                                               CH.sub.2 O                                                                             2-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  CHOCH.sub.3                                  680                                                                               CH.sub.2 O                                                                             3-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  CHOCH.sub.3                                  681                                                                               CH.sub.2 O                                                                             4-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  CHOCH.sub.3                                  682                                                                               CH.sub.2 O                                                                             4-i-C.sub.3 H.sub.7C.sub.6 H.sub.4                                                             CH.sub.3                                                                           H  CHOCH.sub.3                                  683                                                                               CH.sub.2 O                                                                             4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4                                                             CH.sub.3                                                                           H  CHOCH.sub.3                                  684                                                                               CH.sub.2 O                                                                             4-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                               CH.sub.3                                                                           H  CHOCH.sub.3                                  685                                                                               CH.sub.2 O                                                                             2,4-Cl.sub.2C.sub.6 H.sub.3                                                                    CH.sub.3                                                                           H  CHOCH.sub.3                                  686                                                                               CH.sub.2 O                                                                             2,4-(CH.sub.3).sub.4C.sub.6 H.sub.3                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  687                                                                               CH.sub.2 O                                                                             2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2                                                          CH.sub.3                                                                           H  CHOCH.sub.3                                  688                                                                               CH.sub.2 O                                                                             2,4,6-Cl.sub.3C.sub.6 H.sub.2                                                                  CH.sub.3                                                                           H  CHOCH.sub.3                                  689                                                                               CH.sub.2 O                                                                             Pyridin-2-yl    CH.sub.3                                                                           H  CHOCH.sub.3                                  690                                                                               CH.sub.2 O                                                                             Pyridin-3-yl    CH.sub.3                                                                           H  CHOCH.sub.3                                  691                                                                               CH.sub.2 O                                                                             Furan-2-yl      CH.sub.3                                                                           H  CHOCH.sub.3                                  692                                                                               CH.sub.2 O                                                                             6-CH.sub.3 -Pyridin-2-yl                                                                       CH.sub.3                                                                           H  CHOCH.sub.3                                  693                                                                               CH.sub.2 O                                                                             6-Cl-Pyridin-2-yl                                                                              CH.sub.3                                                                           H  CHOCH.sub.3                                  694                                                                               CH.sub.2 O                                                                             Benzothiazol-2-yl                                                                              CH.sub.3                                                                           H  CHOCH.sub.3                                  695                                                                               OCH.sub.2                                                                              H               CH.sub.3                                                                           H  CHOCH.sub.3                                  696                                                                               OCH.sub.2                                                                              C.sub.6 H.sub.5 CH.sub.3                                                                           H  CHOCH.sub.3                                  697                                                                               OCH.sub.2                                                                              2-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           H  CHOCH.sub.3                                  698                                                                               OCH.sub.2                                                                              3-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           H  CHOCH.sub.3                                  699                                                                               OCH.sub.2                                                                              4-FC.sub. 6 H.sub.4                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  700                                                                               OCH.sub.2                                                                              2-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  701                                                                               OCH.sub.2                                                                              3-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  702                                                                               OCH.sub.2                                                                              4-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  703                                                                               OCH.sub.2                                                                              2-BrC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  704                                                                               OCH.sub.2                                                                              3-BrC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  705                                                                               OCH.sub.2                                                                              4-BrC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  706                                                                               OCH.sub.2                                                                              2-IC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           H  CHOCH.sub.3                                  707                                                                               OCH.sub.2                                                                              2-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  CHOCH.sub.3                                  708                                                                               OCH.sub.2                                                                              3-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  CHOCH.sub.3                                  709                                                                               OCH.sub.2                                                                              4-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  CHOCH.sub.3                                  710                                                                               OCH.sub.2                                                                              2-OCH.sub.3C.sub.6 H.sub.4                                                                     CH.sub.3                                                                           H  CHOCH.sub.3                                  711                                                                               OCH.sub.2                                                                              3-OCH.sub.3C.sub.6 H.sub.4                                                                     CH.sub.3                                                                           H  CHOCH.sub.3                                  712                                                                               OCH.sub.2                                                                              4-OCH.sub.3C.sub.6 H.sub.4                                                                     CH.sub.3                                                                           H  CHOCH.sub.3                                  713                                                                               OCH.sub.2                                                                              2-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  CHOCH.sub.3                                  714                                                                               OCH.sub.2                                                                              3-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  CHOCH.sub.3                                  715                                                                               OCH.sub.2                                                                              4-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  CHOCH.sub.3                                  716                                                                               OCH.sub.2                                                                              2-NO.sub.2C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  CHOCH.sub.3                                  717                                                                               OCH.sub.2                                                                              4-NO.sub.2C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  CHOCH.sub.3                                  718                                                                               OCH.sub.2                                                                              2-CH.sub.2 ClC.sub.6 H.sub.4                                                                   CH.sub.3                                                                           H  CHOCH.sub.3                                  719                                                                               OCH.sub.2                                                                              3-CH.sub.2 ClC.sub.6 H.sub.4                                                                   CH.sub.3                                                                           H  CHOCH.sub.3                                  720                                                                               OCH.sub.2                                                                              4-CH.sub.2 ClC.sub.6 H.sub.4                                                                   CH.sub.3                                                                           H  CHOCH.sub.3                                  721                                                                               OCH.sub.2                                                                              2-C.sub.2 H.sub.5C.sub.6 H.sub.4                                                               CH.sub.3                                                                           H  CHOCH.sub.3                                  722                                                                               OCH.sub.2                                                                              3-C.sub.2 H.sub.5C.sub.6 H.sub.4                                                               CH.sub.3                                                                           H  CHOCH.sub.3                                  723                                                                               OCH.sub.2                                                                              4-C.sub.2 H.sub.5C.sub.6 H.sub.4                                                               CH.sub.3                                                                           H  CHOCH.sub.3                                  724                                                                               OCH.sub.2                                                                              3-i-C.sub.3 H.sub.7C.sub.6 H.sub.4                                                             CH.sub.3                                                                           H  CHOCH.sub.3                                  725                                                                               OCH.sub.2                                                                              4-i-C.sub.3 H.sub.7C.sub.6 H.sub.4                                                             CH.sub. 3                                                                          H  CHOCH.sub.3                                  726                                                                               OCH.sub.2                                                                              3-t-C.sub.4 H.sub.9C.sub.6 H.sub.4                                                             CH.sub.3                                                                           H  CHOCH.sub.3                                  727                                                                               OCH.sub.2                                                                              4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4                                                             CH.sub.3                                                                           H  CHOCH.sub.3                                  728                                                                               OCH.sub.2                                                                              3-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                               CH.sub.3                                                                           H  CHOCH.sub.3                                  729                                                                               OCH.sub.2                                                                              4-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                               CH.sub.3                                                                           H  CHOCH.sub.3                                  730                                                                               OCH.sub.2                                                                              4-i-C.sub.3 H.sub.7 OC.sub.6 H.sub.4                                                           CH.sub.3                                                                           H  CHOCH.sub.3                                  731                                                                               OCH.sub.2                                                                              4-t-C.sub.4 H.sub.9 OC.sub.6 H.sub.4                                                           CH.sub.3                                                                           H  CHOCH.sub.3                                  732                                                                               OCH.sub.2                                                                              3-C.sub.6 H.sub.5 OC.sub.6 H.sub.4                                                             CH.sub.3                                                                           H  CHOCH.sub.3                                  733                                                                               OCH.sub.2                                                                              4-C.sub.6 H.sub.5 OC.sub.6 H.sub.4                                                             CH.sub.3                                                                           H  CHOCH.sub.3                                  734                                                                               OCH.sub.2                                                                              3-C.sub.6 H.sub.5 CH.sub.2 OC.sub.6 H.sub.4                                                    CH.sub.3                                                                           H  CHOCH.sub.3                                  735                                                                               OCH.sub.2                                                                              4-C.sub.6 H.sub.5 CH.sub.2 OC.sub.6 H.sub.4                                                    CH.sub.3                                                                           H  CHOCH.sub.3                                  736                                                                               OCH.sub.2                                                                              2,3-Cl.sub.2C.sub.6 H.sub.3                                                                    CH.sub.3                                                                           H  CHOCH.sub.3                                  737                                                                               OCH.sub.2                                                                              2,4-Cl.sub.2C.sub.6 H.sub.3                                                                    CH.sub.3                                                                           H  CHOCH.sub.3                                  738                                                                               OCH.sub.2                                                                              2,5-Cl.sub.2C.sub.6 H.sub.3                                                                    CH.sub.3                                                                           H  CHOCH.sub.3                                  739                                                                               OCH.sub.2                                                                              2,6-Cl.sub.2C.sub.6 H.sub.3                                                                    CH.sub.3                                                                           H  CHOCH.sub.3                                  740                                                                               OCH.sub.2                                                                              2,3,4-Cl.sub.3C.sub.6 H.sub.2                                                                  CH.sub.3                                                                           H  CHOCH.sub.3                                  741                                                                               OCH.sub.2                                                                              2,3,5-Cl.sub.3C.sub.6 H.sub.2                                                                  CH.sub.3                                                                           H  CHOCH.sub.3                                  742                                                                               OCH.sub.2                                                                              2,3,6-Cl.sub.3C.sub.6 H.sub.2                                                                  CH.sub.3                                                                           H  CHOCH.sub.3                                  743                                                                               OCH.sub.2                                                                              C.sub.6 Cl.sub.5                                                                               CH.sub.3                                                                           H  CHOCH.sub.3                                  744                                                                               OCH.sub.2                                                                              C.sub.6 F.sub.5 CH.sub.3                                                                           H  CHOCH.sub.3                                  745                                                                               OCH.sub.2                                                                              2-F, 4-ClC.sub.6 H.sub.4                                                                       CH.sub.3                                                                           H  CHOCH.sub.3                                  746                                                                               OCH.sub.2                                                                              4-F, 2-ClC.sub.6 H.sub.3                                                                       CH.sub.3                                                                           H  CHOCH.sub.3                                  747                                                                               OCH.sub.2                                                                              2-CH.sub.3, 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.3                                                 CH.sub.3                                                                           H  CHOCH.sub.3                                  748                                                                               OCH.sub.2                                                                              2-CH.sub.3, 4-Cyclohexyl-C.sub.6 H.sub.3                                                       CH.sub.3                                                                           H  CHOCH.sub.3                                  749                                                                               OCH.sub.2                                                                              2-CH.sub.2, 4-i-C.sub.3 H.sub.7, C.sub.6 H.sub.3                                               CH.sub.3                                                                           H  CHOCH.sub.3                                  750                                                                               OCH.sub.2                                                                              2,3-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  761                                                                               OCH.sub.2                                                                              2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  762                                                                               OCH.sub.2                                                                              2,5-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  763                                                                               OCH.sub.2                                                                              2,3,5-(CH.sub.3).sub.3C.sub.6 H.sub.2                                                          CH.sub.3                                                                           H  CHOCH.sub.3                                  764                                                                               OCH.sub.2                                                                              2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2                                                          CH.sub.3                                                                           H  CHOCH.sub.3                                  765                                                                               OCH.sub.2                                                                              3,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  766                                                                               OCH.sub.2                                                                              3,5-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  767                                                                               OCH.sub.2                                                                              3,5-(C.sub.2 H.sub.5).sub.2C.sub.6 H.sub.3                                                     CH.sub.3                                                                           H  CHOCH.sub.3                                  768                                                                               OCH.sub.2                                                                              4-Cyclohexyl-C.sub.6 H.sub.4                                                                   CH.sub.3                                                                           H  CHOCH.sub.3                                  769                                                                               OCH.sub.2                                                                              CH.sub.2 CHCH.sub.2                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  770                                                                               OCH.sub.2                                                                              CH.sub.2CHCHCH.sub.3                                                                           CH.sub.3                                                                           H  CHOCH.sub.3                                  771                                                                               OCH.sub.2                                                                              CH.sub.2CHC(CH.sub.3).sub.2                                                                    CH.sub.3                                                                           H  CHOCH.sub.3                                  772                                                                               OCH.sub.2                                                                              CH.sub.2C(CH.sub.3)CH.sub.2                                                                    CH.sub.3                                                                           H  CHOCH.sub.3                                  773                                                                               OCH.sub.2                                                                              CH.sub.2C.sub.6 H.sub.5                                                                        CH.sub.3                                                                           H  CHOCH.sub.3                                  774                                                                               OCH.sub.2                                                                              Cyclohexyl      CH.sub.3                                                                           H  CHOCH.sub.3                                  775                                                                               OCH.sub.2                                                                              CH.sub.2CCH     CH.sub.3                                                                           H  CHOCH.sub.3                                  776                                                                               OCH.sub.2                                                                              CH.sub.2 CHCHC.sub.6 H.sub.5                                                                   CH.sub.3                                                                           H  CHOCH.sub.3                                  777                                                                               OCH.sub.2                                                                              CH.sub.2 CH.sub.2OC.sub.6 H.sub.5                                                              CH.sub.3                                                                           H  CHOCH.sub.3                                  778                                                                               O       H               CH.sub.3                                                                           H  CHOCH.sub.3                                  779                                                                               O       C.sub.6 H.sub.5 CH.sub.3                                                                           H  CHOCH.sub.3                                  780                                                                               O       3-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                               CH.sub.3                                                                           H  CHOCH.sub.3                                  781                                                                               O       3-n-C.sub.3 H.sub.7 OC.sub.6 H.sub.4                                                           CH.sub.3                                                                           H  CHOCH.sub.3                                  782                                                                               O       Pyridin-2-yl    CH.sub.3                                                                           H  CHOCH.sub.3                                  783                                                                               O       6-C.sub.6 H.sub.5 -Pyridin-2-yl                                                                CH.sub.3                                                                           H  CHOCH.sub.3                                  784                                                                               O       CH.sub.2CHCH.sub.2                                                                             CH.sub.3                                                                           H  CHOCH.sub.3                                  785                                                                               O       3-C.sub.6 H.sub.5 OC.sub.6 H.sub.4                                                             CH.sub.3                                                                           H  CHOCH.sub.3                                  786                                                                               O       3-C.sub.6 H.sub.5 SC.sub.6 H.sub.4                                                             CH.sub.3                                                                           H  CHOCH.sub.3                                  787                                                                               O       3-C.sub.6 H.sub.5CH.sub.2 OC.sub.6 H.sub.4                                                     CH.sub.3                                                                           H  CHOCH.sub.3                                  788                                                                               O       4-C.sub.6 H.sub.5 OC.sub.6 H.sub.4                                                             CH.sub.3                                                                           H  CHOCH.sub.3                                  789                                                                               O       5-C.sub.6 H.sub.5 OCH.sub.2C.sub.6 H.sub.4                                                     CH.sub.3                                                                           H  CHOCH.sub.3                                  790                                                                               CC      CH.sub.3        CH.sub.3                                                                           H  CHOCH.sub.3                                  791                                                                               CC      C.sub.6 H.sub.5 CH.sub.3                                                                           H  CHOCH.sub.3                                  792                                                                               S       C.sub.6 H.sub.5 CH.sub.3                                                                           H  CHOCH.sub.3                                  793                                                                               S       2-ClC.sub.6 H.sub.5                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  794                                                                               SCH.sub.2                                                                              C.sub.6 H.sub.5 CH.sub.3                                                                           H  CHOCH.sub.3                                  795                                                                               SCH.sub.2                                                                              2-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  796                                                                               SCH.sub.2                                                                              4-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  797                                                                               SCH.sub.2                                                                              4-FC.sub.6 H.sub.4                                                                             CH.sub.3                                                                           H  CHOCH.sub.3                                  798                                                                               SCH.sub.2                                                                              4-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  CHOCH.sub.3                                  799                                                                               SCH.sub.2                                                                              6-CH.sub.3 -Pyridin-2-yl                                                                       CH.sub.3                                                                           H  CHOCH.sub.3                                  800                                                                               SCH.sub.2                                                                              6-Cl-Pyridin-2-yl                                                                              CH.sub.3                                                                           H  CHOCH.sub.3                                  801                                                                               SCH.sub.2                                                                              Benzothiazol-2-yl                                                                              CH.sub.3                                                                           H  CHOCH.sub.3                                  802                                                                               SCH.sub.2                                                                              5-Cl-Benzothiazol-2-yl                                                                         CH.sub.3                                                                           H  CHOCH.sub.3                                  803                                                                               SCH.sub.2                                                                              6-Cl-Benzothiazol-2-yl                                                                         CH.sub.3                                                                           H  CHOCH.sub.3                                  804                                                                               SCH.sub.2                                                                              4,8-(CH.sub.3).sub.2 -quinolin-2-yl                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  805                                                                               COO     CH.sub.3        CH.sub.3                                                                           H  CHOCH.sub.3                                  806                                                                               COO     C.sub.6 H.sub.5 CH.sub.3                                                                           H  CHOCH.sub.3                                  807                                                                               OCO     CH.sub.3        CH.sub.3                                                                           H  CHOCH.sub.3                                  808                                                                               OCO     C.sub.6 H.sub.5 CH.sub.3                                                                           H  CHOCH.sub.3                                  809                                                                               OCO     CH.sub.2 C.sub.6 H.sub.5                                                                       CH.sub.3                                                                           H  CHOCH.sub.3                                  810                                                                               OCO     H               CH.sub.3                                                                           H  CHOCH.sub.3                                  811                                                                               COCH.sub.2                                                                             H               CH.sub.3                                                                           H  CHOCH.sub.3                                  812                                                                               COCH.sub.2                                                                             CH.sub.3        CH.sub.3                                                                           H  CHOCH.sub.3                                  813                                                                               COCH.sub.2                                                                             C.sub.6 H.sub.5 CH.sub.3                                                                           H  CHOCH.sub.3                                  814                                                                               COCH.sub.2                                                                             2-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.3                                                                           H  CHOCH.sub.3                                  815                                                                               COCH.sub.2                                                                             2,4-(CH.sub.3).sub.2C.sub.6 H.sub.4                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  816                                                                               COCH.sub.2                                                                             2-ClC.sub.6 H.sub.4                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  817                                                                               CH.sub.2CO                                                                             H               CH.sub.3                                                                           H  CHOCH.sub.3                                  818                                                                               CH.sub.2CO                                                                             C.sub.6 H.sub.5 CH.sub.3                                                                           H  CHOCH.sub.3                                  819                                                                               NN      C.sub.6 H.sub.5 CH.sub.3                                                                           H  CHOCH.sub.3                                  820                                                                               COOCH.sub.2                                                                            CH.sub.3        CH.sub.3                                                                           H  CHOCH.sub.3                                  821                                                                               COOCH.sub.2                                                                            tert.-C.sub.4 H.sub.9                                                                          CH.sub.3                                                                           H  CHOCH.sub.3                                  822                                                                               COOCH.sub.2                                                                            1-Methyl-cyclopropyl                                                                           CH.sub.3                                                                           H  CHOCH.sub.3                                  823                                                                               COOCH.sub.2                                                                            2,2-Dichlorocyclopropyl                                                                        CH.sub.3                                                                           H  CHOCH.sub.3                                  824                                                                               COOCH.sub.2                                                                            2-Phenylcyclopropyl                                                                            CH.sub.3                                                                           H  CHOCH.sub.3                                  825                                                                               COOCH.sub.2                                                                            1-(2-Chlorophenyl)cyclopropyl                                                                  CH.sub.3                                                                           H  CHOCH.sub.3                                  826                                                                               CH.sub.2                                                                               H               CH.sub.3                                                                           H  CHOCH.sub.3                                  827                                                                               CHCl    H               CH.sub.3                                                                           H  CHOCH.sub.3                                  828                                                                               CHBr    H               CH.sub.3                                                                           H  CHOCH.sub.3                                  829                                                                               CH.sub.2 CH.sub.2                                                                      C.sub.6 H.sub.5 C.sub.2 H.sub.5                                                                    H  CHOCH.sub.3                                  830                                                                               CHCH    C.sub.6 H.sub.5 C.sub.2 H.sub.5                                                                    H  CHOCH.sub.3                                  831                                                                               OCH.sub.2                                                                              C.sub.6 H.sub.5 C.sub.2 H.sub.5                                                                    H  CHOCH.sub.3                                  832                                                                               CH.sub.2 O                                                                             C.sub.6 H.sub.5 C.sub.2 H.sub.5                                                                    H  CHOCH.sub.3                                  833                                                                               O       C.sub.6 H.sub.5 C.sub.2 H.sub.5                                                                    H  CHOCH.sub.3                                  834                                                                               OCH.sub.2                                                                              C.sub.6 H.sub.5 OCH.sub.3                                                                          H  CHOCH.sub.3                                  835                                                                               CHCH    C.sub.6 H.sub.5 OCH.sub.3                                                                          H  CHOCH.sub.3                                  836                                                                               CH.sub.2                                                                               H               OCH.sub.3                                                                          H  CHOCH.sub.3                                  837                                                                               CHCl    H               OCH.sub.3                                                                          H  CHOCH.sub.3                                  838                                                                               CHBr    H               OCH.sub.3                                                                          H  CHOCH.sub.3                                  839                                                                               CH.sub.2                                                                               H               OCH.sub.3                                                                          CH.sub.3                                                                          CHOCH.sub.3                                  840                                                                               OCH.sub.2                                                                              C.sub.6 H.sub.5 OCH.sub.3                                                                          CH.sub.3                                                                          CHOCH.sub.3                                  841                                                                               OCH.sub.2                                                                              C.sub.6 H.sub.5 OC.sub.2 H.sub.5                                                                   H  CHOCH.sub.3                                  842                                                                               CH.sub.2 CH.sub.2                                                                      C.sub.6 H.sub.5 H   H  CHOMe                                        843                                                                               CHCH    C.sub.6 H.sub.5 H   H  CHOMe                                        844                                                                               CH.sub.2                                                                               C.sub.6 H.sub.5 H   H  CHOMe                                        845                                                                               OCH.sub.2                                                                              C.sub.6 H.sub.5 H   H  CHOMe                                        846                                                                               O       C.sub.6 H.sub.5 H   H  CHOMe                                        847                                                                               C C     C.sub.6 H.sub.5 H   H  CHOMe                                        848                                                                               S       C.sub.6 H.sub.5 H   H  CHOMe                                        849                                                                               SCH.sub.2                                                                              C.sub.6 H.sub.5 H   H  CHOMe                                        850                                                                               COO     C.sub.6 H.sub.5 H   H  CHOMe                                        851                                                                               OCO     C.sub.6 H.sub.5 H   H  CHOMe                                        852                                                                               COCH.sub.2                                                                             C.sub.6 H.sub.5 H   H  CHOMe                                        853                                                                               CH.sub.2CO                                                                             C.sub.6 H.sub.5 H   H  CHOMe                                        854                                                                               CH.sub.2 CH.sub.2                                                                      C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          CHOMe                                        855                                                                               CHCH    C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          CHOMe                                        856                                                                               CH.sub.2 O                                                                             C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          CHOMe                                        857                                                                               OCH.sub.2                                                                              C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          CHOMe                                        858                                                                               O       C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          CHOMe                                        859                                                                               CC      C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          CHOMe                                        860                                                                               S       C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          CHOMe                                        861                                                                               SCH.sub.2                                                                              C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          CHOMe                                        862                                                                               COO     C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          CHOMe                                        863                                                                               OCO     C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          CHOMe                                        864                                                                               COCH.sub.2                                                                             C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          CHOMe                                        865                                                                               CH.sub.2CO                                                                             C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          CHOMe                                        866                                                                               OCH.sub.2                                                                              C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          CHOMe                                        867                                                                               OCH.sub.2                                                                              C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          CHOMe                                        868                                                                               CH.sub.2 CH.sub.2                                                                      C.sub.6 H.sub.5 H   H  CHSCH.sub.3                                  869                                                                               CHCH    C.sub.6 H.sub.5 H   H  CHSCH.sub.3                                  870                                                                               CH.sub.2 O                                                                             C.sub.6 H.sub.5 H   H  CHSCH.sub.3                                  871                                                                               OCH.sub.2                                                                              C.sub.6 H.sub.5 H   H  CHSCH.sub.3                                  872                                                                               O       C.sub.6 H.sub.5 H   H  CHSCH.sub.3                                  873                                                                               CH.sub.2 CH.sub.2                                                                      C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          CHSCH.sub.3                                  874                                                                               CHCH    C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          CHSCH.sub.3                                  875                                                                               CH.sub.2 O                                                                             C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          CHSCH.sub.3                                  876                                                                               OCH.sub.2                                                                              C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          CHSCH.sub.3                                  877                                                                               O       C.sub.6 H.sub.5 CH.sub.3                                                                           CH.sub.3                                                                          CHSCH.sub.3                                  878                                                                               CH.sub.2 CH.sub.2                                                                      C.sub.6 H.sub.5 CH.sub.3                                                                           H  CHSCH.sub.3                                  879                                                                               CHCH    C.sub.6 H.sub.5 CH.sub.3                                                                           H  CHSCH.sub.3                                  880                                                                               CH.sub.2 O                                                                             C.sub.6 H.sub.5 CH.sub.3                                                                           H  CHSCH.sub.3                                  881                                                                               OCH.sub.2                                                                              C.sub.6 H.sub.5 CH.sub.3                                                                           H  CHSCH.sub.3                                  882                                                                               O       C.sub.6 H.sub.5 CH.sub.3                                                                           H  CHSCH.sub.3                                  883                                                                               COOCH.sub.2                                                                            1-Methylcyclopropyl                                                                            CH.sub.3                                                                           H  CHSCH.sub.3                                  884                                                                               CC      C.sub.6 H.sub.5 CH.sub.3                                                                           H  CHSCH.sub.3                                  885                                                                               S       C.sub.6 H.sub.5 CH.sub.3                                                                           H  CHSCH.sub.3                                  886                                                                               SCH.sub.2                                                                              C.sub.6 H.sub.5 CH.sub.3                                                                           H  CHSCH.sub.3                                  887                                                                               COO     C.sub.6 H.sub.5 CH.sub.3                                                                           H  CHSCH.sub.3                                  888                                                                               OCO     C.sub.6 H.sub.5 CH.sub.3                                                                           H  CHSCH.sub.3                                  889                                                                               COCH.sub.2                                                                             C.sub.6 H.sub.5 CH.sub.3                                                                           H  CHSCH.sub.3                                  890                                                                               CH.sub.2CO                                                                             C.sub.6 H.sub.5 CH.sub.3                                                                           H  CHSCH.sub.3                                  891                                                                               OCH.sub.2                                                                              C.sub.6 H.sub.5 OCH.sub.3                                                                          H  CHSCH.sub.3                                  892                                                                               OCH.sub.2                                                                              C.sub.6 H.sub.5 OCH.sub.3                                                                          CH.sub.3                                                                          CHSCH.sub.3                                  __________________________________________________________________________

EXAMPLES OF USE

The comparison substance was ##STR12## which is disclosed in EP-A 310 954 (compound No. 312; E/Z isomer mixture)

EXAMPLE 5

Activity against Plasmopara viticola

Leaves of potted vines of the Muller-Thurgau variety were sprayed with 0.025% by weight aqueous suspensions containing 80% by weight active ingredient (Examples 87, 89, 93, 96, 242, 252, 449, 494, 585 and 586 in the table) and 20% by weight emulsifier in dry matter. To assess the duration of action after the sprayed-on layer had dried, the plants were placed in a greenhouse for 8 days. The leaves were then infected with a suspension of Plasmopara viticola spores and the plants were placed in a chamber saturated with water vapor at 24°°C. for 48 hours. The vines were then grown in a greenhouse at from 20° to 30° C. for 5 days and, to accelerate sporangiophore for discharge, again placed in the humidity chamber for 16 hours. The extent of the fungus attack was then assessed on the undersides of the leaves.

Compared with a control test (no treatment, 60% fungus attack) and the known comparison compound A (35% fungus attack) it was found that the fungus attack was only from 0 to 5% on the plants treated with active ingredients 87, 89, 93, 96, 242, 252, 449, 494, 585 and 586.

EXAMPLE 6

Activity against wheat mildew

Leaves of pot-grown wheat seedlings of the Fruhgold variety were sprayed with 0.025% by weight aqueous formulations which contained 80% by weight active ingredient (Examples 449 and 587 in the table) and 20% by weight emulsifier in dry matter, and, 24 hours after the sprayed-on layer had dried, dusted with spores of wheat mildew (Erysiphe graminis var. tritici). The test plants were then placed in a greenhouse at from 20° to 22° C. and 75 to 80% relative humidity. The extent of mildew development was assessed after 7 days.

Compared with a control test (no treatment, 70% fungus attack) and the known comparison compound A (35% fungus attack) it was found that plants treated with active ingredients 449 and 587 had no fungus attack.

EXAMPLE 7

Activity against Pyricularia oryzae (preventive treatment)

Leaves of pot-grown rice seedlings of the Bahia variety were sprayed to run off with aqueous emulsions which contained 80% active ingredient and 20% emulsifier in dry matter and, 24 hours later, infected with an aqueous suspension of Pyricularia oryzae spores. The test plants were then placed in chambers at from 20° to 24° C. and 95 to 99% relative humidity. The extent of fungus attack was determined after 6 days.

The results shows that active ingredients 242, 252, 449, 585 and 588 when used as 0.05% by weight aqueous formulation have a much better fungicidal action (93%) than the known comparison substance A (20%). 

We claim:
 1. A method for controlling fungi, which comprises exposing the fungi, the plants threatened by fungal attack, their habitat or the seed of the threatened plants to a fungicidally effective amount of a compound of the formula ##STR13## wherein (X)_(m) is selected from the group consisting of: (a) one C₁ -C₄ -alkyl group, the said group being at position 2;(b) two independently selected C₁ -C₄ -alkyl groups, wherein at least one of the alkyl groups is at 2-position; and (c) three independently selected C₁ -C₄ -alkyl groups, wherein at least one of the alkyl groups is at 2-position; Y is --OCH₂ -- W is N--OC₁ -C₄ -alkyl; and each of R⁴ and R⁵ is independently selected from the group consisting of hydrogen and C₁ -C₄ -alkyl.
 2. The method of claim 1, wherein the compound is 2-methoximino-2-[(2,4-dimethylphenoxymethyl)phenyl]-acetic acid N-methylamide.
 3. The method of claim 1, wherein the compound is 2-methoximino-2-[(2,5-dimethylphenoxymethyl)phenyl]-acetic acid N-methylamide.
 4. The method of claim 1, wherein the compound is 2-methoximino-2-[(2,3,5-trimethylphenoxymethyl)phenyl]-acetic acid N-methylamide.
 5. The method of claim 1, wherein the compound is 2-methoximino-2-[(2-methylphenoxymethyl)phenyl]-acetic acid N-methylamide. 